Substituted Pyrazolecarboxylic Acid Anilide Derivative or Salt Thereof, Intermediate Thereof, Agent for Agricultural and Horticultural Use, and Use Thereof

ABSTRACT

The substituted pyrazolecarboxanilide derivatives represented by of the formula (I) 
     
       
         
         
             
             
         
       
     
     wherein R 1  is H, alkyl, alkylcarbonyl, alkenylcarbonyl, cycloalkyl, phenylalkyl, phenylcarbonyl and the like; R 2  is H, halogen, alkyl, CN, OH, alkoxy, phenoxy, phenylthio, phenylsulfonyl and the like; G is alkyl, alkenyl, alkynyl, cycloalkyl, C 3 -C 10  cycloalkenyl and the like; Z is O or S; X is H, halogen, CN, NO 2 , alkyl and the like; Y 1  is H, alkyl, alkenyl, phenyl, alkoxyalkyl and the like; Y 2  is H, halogen, CN, NO 2 , OH, mercapto, amino, carboxyl, C 1 -C 6  alkyl, phenyl, phenoxy, heterocycle and the like, m is 1 or 2; and n is 1-3, and salts thereof exhibit a superior effect as agrohorticultural insecticides or acaricides.

TECHNICAL FIELD

The present invention relates to substituted pyrazolecarboxanilidederivatives or salts thereof, intermediates thereof, andagrohorticultural agents, particularly insecticides or acaricides,containing said compounds as an active ingredient and method for usethereof.

BACKGROUND ART

Conventionally, substituted pyrazolecarboxamide derivatives similar tothe present invention are known to be useful as agrohorticulturalinsecticides, fungicides or acaricides (e.g., JP-A-2003-48878,JP-A-2004-189738 and JP-A-2004-269515). In JP-A-2003-48878, thesubstituted pyrazolecarboxanilide derivatives are disclosed. However,the substituents in the aniline moiety are mostly limited to the2-position substituents, the 3-position substituent is methyl groupalone, and the compound described in the present invention, whereinalkyl group having 2 or more carbon atoms is introduced into the3-position is not included even in its compound list. Moreover, the3-position methyl form concretely disclosed therein does not show anacaricide activity. In JP-A-2004-189738, substitutedpyrazolecarboxanilide derivatives are disclosed. However, thesubstituents in the aniline moiety are limited to alkoxy group,alkylthio group and alkylamino group, and the compound described in thepresent invention, wherein alkyl group having 2 or more carbon atoms isdirectly introduced into the 3-position is not included even in itscompound list. In JP-A-2004-269515, substituted pyrazolecarboxamidederivatives are disclosed. However, only an amide compound withheterocyclyl amine is disclosed, and the substitutedpyrazolecarboxanilide derivatives of the present invention are notdisclosed.

DISCLOSURE OF THE INVENTION

In crop manufacturing in agricultural and horticultural fields, damagescaused by insect pests are still serious, and development of novelagrohorticultural agents, particularly development of insecticides andacaricides is desired due to generation of insect pests resistant toknown agents, and the like. Since various labor saving farm works arerequired due to increasing numbers of the aged farm working population,creation of agrohorticultural agents with properties suitable for suchlabor saving farm works, particularly insecticides and acaricides, isalso demanded.

The present inventors have continued extensive studies on development ofnovel agrohorticultural agents, particularly insecticides and acaricidesand have found, as the result, that among broad range of compoundsdescribed in the aforementioned prior document, a substitutedpyrazolecarboxanilide derivative represented by the formula (I), inwhich a pyrazole ring is selected as the heterocyclic carboxylic acidmoiety and a specific substituent is introduced into the aniline moietyat 3-position, showed excellent control effect as acaricides, notpredicted at all from the content described in the aforementioned priorart references. Further, the inventors have found that an intermediateof said compound, i.e. a substituted aniline derivatives represented bythe formula (II), and1,3-dimethyl-5-trifluoromethylpyrazole-4-carboxylic acid or salt thereofwere novel compounds unknown in prior references, and were useful asintermediates for manufacturing various derivatives having physiologicalactivities such as pharmaceuticals, pesticides and the like, and thuscompleted the present invention.

Accordingly, the present invention relates to substitutedpyrazolecarboxanilide derivatives represented by the formula (I):

whereinR¹ is 1a) a hydrogen atom, 2a) a C₁-C₈ alkyl group, 3a) a halo C₁-C₆alkyl group, 4a) a C₁-C₆ alkylcarbonyl group, 5a) a halo C₁-C₆alkylcarbonyl group, 6a) a C₂-C₆ alkenylcarbonyl group, 7a) a halo C₂-C₆alkenylcarbonyl group, 8a) a C₁-C₆ alkylcarbonyl C₁-C₆ alkyl group, 9a)a C₃-C₆ cycloalkyl group, 10a) a halo C₃-C₆ cycloalkyl group, 11a) aC₃-C₆ cycloalkyl C₁-C₆ alkyl group, 12a) a halo C₃-C₆ cycloalkyl C₁-C₆alkyl group, 13a) a C₂-C₆ alkenyl group, 14a) a halo C₂-C₆ alkenylgroup, 15a) a C₂-C₆ alkynyl group, 16a) a halo C₂-C₆ alkynyl group, 17a)a C₁-C₁₀ alkoxy C₁-C₆ alkyl group, 18a) a halo C₁-C₆ alkoxy C₁-C₆ alkylgroup, 19a) a C₂-C₆ alkenyloxy C₁-C₆ alkyl group, 20a) a C₁-C₆ alkoxyC₁-C₆ alkoxy C₁-C₆ alkyl group, 21a) a C₁-C₆ alkylthio C₁-C₆ alkylgroup, 22a) a halo C₁-C₆ alkylthio C₁-C₆ alkyl group, 23a) a C₁-C₆alkylsulfinyl C₁-C₆ alkyl group, 24a) a halo C₁-C₆ alkylsulfinyl C₁-C₆alkyl group, 25a) a C₁-C₆ alkylsulfonyl C₁-C₆ alkyl group, 26a) a haloC₁-C₆ alkylsulfonyl C₁-C₆ alkyl group, 27a) a mono C₁-C₆ alkylaminoC₁-C₆ alkyl group, 28a) a di C₁-C₆ alkylamino C₁-C₆ alkyl group whereinthe alkyl groups are the same or different, 29a) a phenyl C₁-C₆ alkoxyC₁-C₆ alkyl group, 30a) a substituted phenyl C₁-C₆ alkoxy C₁-C₆ alkylgroup having, on the ring, one or more, the same or differentsubstituents selected from a) a halogen atom, b) a cyano group, c) anitro group, d) a C₁-C₆ alkyl group, e) a halo C₁-C₆ alkyl group, f) aC₁-C₆ alkoxy group, g) a halo C₁-C₆ alkoxy group, h) a C₁-C₆ alkylthiogroup, i) a halo C₁-C₆ alkylthio group, j) a C₁-C₆ alkylsulfinyl group,k) a halo C₁-C₆ alkylsulfinyl group, l) a C₁-C₆ alkylsulfonyl group, m)a halo C₁-C₆ alkylsulfonyl group, n) a mono C₁-C₆ alkylamino group, o) adi C₁-C₆ alkylamino group wherein the alkyl groups are the same ordifferent, and p) a C₁-C₆ alkoxycarbonyl group, 31a) a C₁-C₁₆alkoxycarbonyl group, 32a) a C₁-C₆ alkoxy C₁-C₆ alkoxycarbonyl group,33a) a halo C₁-C₆ alkoxycarbonyl group, 34a) a C₂-C₆ alkenyloxycarbonylgroup, 35a) a C₁-C₆ alkylthiocarbonyl group, 36a) a mono C₁-C₆alkylaminocarbonyl group, 37a) a di C₁-C₆ alkylaminocarbonyl groupwherein the alkyl groups are the same or different, 38a) a C₁-C₆alkoxycarbonyl C₁-C₆ alkyl group, 39a) a C₁-C₆ alkylsulfonyl group, 40a)a halo C₁-C₆ alkylsulfonyl group, 41a) a cyano C₁-C₆ alkyl group, 42a) aphenyl C₁-C₆ alkyl group, 43a) a substituted phenyl C₁-C₆ alkyl grouphaving, on the ring, one or more, the same or different substituentsselected from a) a halogen atom, b) a cyano group, c) a nitro group, d)a C₁-C₆ alkyl group, e) a halo C₁-C₆ alkyl group, f) a C₁-C₆ alkoxygroup, g) a halo C₁-C₆ alkoxy group, h) a C₁-C₆ alkylthio group, i) ahalo C₁-C₆ alkylthio group, j) a C₁-C₆ alkylsulfinyl group, k) a haloC₁-C₆ alkylsulfinyl group, l) a C₁-C₆ alkylsulfonyl group, m) a haloC₁-C₆ alkylsulfonyl group, n) a mono C₁-C₆ alkylamino group, o) a diC₁-C₆ alkylamino group wherein the alkyl groups are the same ordifferent, and p) a C₁-C₆ alkoxycarbonyl group, 44a) a phenylcarbonylgroup, 45a) a substituted phenylcarbonyl group having, on the ring, oneor more, the same or different substituents selected from a) a halogenatom, b) a cyano group, c) a nitro group, d) a C₁-C₆ alkyl group, e) ahalo C₁-C₆ alkyl group, f) a C₁-C₆ alkoxy group, g) a halo C₁-C₆ alkoxygroup, h) a C₁-C₆ alkylthio group, i) a halo C₁-C₆ alkylthio group, j) aC₁-C₆ alkylsulfinyl group, k) a halo C₁-C₆ alkylsulfinyl group, l) aC₁-C₆ alkylsulfonyl group, m) a halo C₁-C₆ alkylsulfonyl group, n) amono C₁-C₆ alkylamino group, o) a di C₁-C₆ alkylamino group wherein thealkyl groups are the same or different, and p) a C₁-C₆ alkoxycarbonylgroup, 46a) a heterocyclylcarbonyl group, 47a) a substitutedheterocyclylcarbonyl group having, on the ring, one or more, the same ordifferent substituents selected from a) a halogen atom, b) a cyanogroup, c) a nitro group, d) a C₁-C₆ alkyl group, e) a halo C₁-C₆ alkylgroup, f) a C₁-C₆ alkoxy group, g) a halo C₁-C₆ alkoxy group, h) a C₁-C₆alkylthio group, i) a halo C₁-C₆ alkylthio group, j) a C₁-C₆alkylsulfinyl group, k) a halo C₁-C₆ alkylsulfinyl group, l) a C₁-C₆alkylsulfonyl group, m) a halo C₁-C₆ alkylsulfonyl group, n) a monoC₁-C₆ alkylamino group, o) a di C₁-C₆ alkylamino group wherein the alkylgroups are the same or different, and p) a C₁-C₆ alkoxycarbonyl group,48a) a phenoxycarbonyl group, 49a) a substituted phenoxycarbonyl grouphaving, on the ring, one or more, the same or different substituentsselected from a) a halogen atom, b) a cyano group, c) a nitro group, d)a C₁-C₆ alkyl group, e) a halo C₁-C₆ alkyl group, f) a C₁-C₆ alkoxygroup, g) a halo C₁-C₆ alkoxy group, h) a C₁-C₆ alkylthio group, i) ahalo C₁-C₆ alkylthio group, j) a C₁-C₆ alkylsulfinyl group, k) a haloC₁-C₆ alkylsulfinyl group, l) a C₁-C₆ alkylsulfonyl group, m) a haloC₁-C₆ alkylsulfonyl group, n) a mono C₁-C₆ alkylamino group, o) a diC₁-C₆ alkylamino group wherein the alkyl groups are the same ordifferent, and p) a C₁-C₆ alkoxycarbonyl group, 50a) a phenoxy C₁-C₆alkylcarbonyl group, 51a) a substituted phenoxy C₁-C₆ alkylcarbonylgroup having, on the ring, one or more, the same or differentsubstituents selected from a) a halogen atom, b) a cyano group, c) anitro group, d) a C₁-C₆ alkyl group, e) a halo C₁-C₆ alkyl group, f) aC₁-C₆ alkoxy group, g) a halo C₁-C₆ alkoxy group, h) a C₁-C₆ alkylthiogroup, i) a halo C₁-C₆ alkylthio group, j) a C₁-C₆ alkylsulfinyl group,k) a halo C₁-C₆ alkylsulfinyl group, l) a C₁-C₆ alkylsulfonyl group, m)a halo C₁-C₆ alkylsulfonyl group, n) a mono C₁-C₆ alkylamino group, o) adi C₁-C₆ alkylamino group wherein the alkyl groups are the same ordifferent, and p) a C₁-C₆ alkoxycarbonyl group, 52a) a phenylsulfonylgroup, 53a) a substituted phenylsulfonyl group having, on the ring, oneor more, the same or different substituents selected from a) a halogenatom, b) a cyano group, c) a nitro group, d) a C₁-C₆ alkyl group, e) ahalo C₁-C₆ alkyl group, f) a C₁-C₆ alkoxy group, g) a halo C₁-C₆ alkoxygroup, h) a C₁-C₆ alkylthio group, i) a halo C₁-C₆ alkylthio group, j) aC₁-C₆ alkylsulfinyl group, k) a halo C₁-C₆ alkylsulfinyl group, l) aC₁-C₆ alkylsulfonyl group, m) a halo C₁-C₆ alkylsulfonyl group, n) amono C₁-C₆ alkylamino group, o) a di C₁-C₆ alkylamino group wherein thealkyl groups are the same or different, and p) a C₁-C₆ alkoxycarbonylgroup, 54a) a di C₁-C₆ alkylphosphono group wherein the alkyl groups arethe same or different, 55a) a di C₁-C₆ alkylphosphonothio group whereinthe alkyl groups are the same or different, 56a) a N—C₁-C₆ alkyl-N—C₁-C₆alkoxycarbonylaminothio group, 57a) a N—C₁-C₆ alkyl-N—C₁-C₆alkoxycarbonyl C₁-C₆ alkylaminothio group, 58a) a di C₁-C₆alkylaminothio group wherein the alkyl groups are the same or different,59a) a C₃-C₆ cycloalkylcarbonyl group, 60a) a halo C₃-C₆cycloalkylcarbonyl group, 61a) a C₁-C₆ alkyl C₃-C₆ cycloalkylcarbonylgroup, 62a) a halo C₁-C₆ alkyl C₃-C₆ cycloalkylcarbonyl group, 63a) aphenyl C₁-C₆ alkylcarbonyl group, 64a) a substituted phenyl C₁-C₆alkylcarbonyl group having, on the ring, one or more, the same ordifferent substituents selected from a) a halogen atom, b) a cyanogroup, c) a nitro group, d) a C₁-C₆ alkyl group, e) a halo C₁-C₆ alkylgroup, f) a C₁-C₆ alkoxy group, g) a halo C₁-C₆ alkoxy group, h) a C₁-C₆alkylthio group, i) a halo C₁-C₆ alkylthio group, j) a C₁-C₆alkylsulfinyl group, k) a halo C₁-C₆ alkylsulfinyl group, l) a C₁-C₆alkylsulfonyl group, m) a halo C₁-C₆ alkylsulfonyl group, n) a monoC₁-C₆ alkylamino group, o) a di C₁-C₆ alkylamino group wherein the alkylgroups are the same or different, and p) a C₁-C₆ alkoxycarbonyl group,65a) a phenyl C₃-C₆ cycloalkylcarbonyl group, 66a) a substituted phenylC₃-C₆ cycloalkylcarbonyl group having, on the ring, one or more, thesame or different substituents selected from a) a halogen atom, b) acyano group, c) a nitro group, d) a C₁-C₆ alkyl group, e) a halo C₁-C₆alkyl group, f) a C₁-C₆ alkoxy group, g) a halo C₁-C₆ alkoxy group, h) aC₁-C₆ alkylthio group, i) a halo C₁-C₆ alkylthio group, j) a C₁-C₆alkylsulfinyl group, k) a halo C₁-C₆ alkylsulfinyl group, l) a C₁-C₆alkylsulfonyl group, m) a halo C₁-C₆ alkylsulfonyl group, n) a monoC₁-C₆ alkylamino group, o) a di C₁-C₆ alkylamino group wherein the alkylgroups are the same or different, and p) a C₁-C₆ alkoxycarbonyl group,67a) a C₃-C₆ cycloalkyl C₁-C₆ alkylcarbonyl group, 68a) a C₁-C₆ alkoxyC₁-C₆ alkylcarbonyl group, 69a) a halo C₃-C₆ cycloalkyl C₁-C₆alkylcarbonyl group, 70a) a phenoxy C₁-C₆ alkoxycarbonyl group, 71a) asubstituted phenoxy C₁-C₆ alkoxycarbonyl group having, on the ring, oneor more, the same or different substituents selected from a) a halogenatom, b) a cyano group, c) a nitro group, d) a C₁-C₆ alkyl group, e) ahalo C₁-C₆ alkyl group, f) a C₁-C₆ alkoxy group, g) a halo C₁-C₆ alkoxygroup, h) a C₁-C₆ alkylthio group, i) a halo C₁-C₆ alkylthio group, j) aC₁-C₆ alkylsulfinyl group, k) a halo C₁-C₆ alkylsulfinyl group, l) aC₁-C₆ alkylsulfonyl group, m) a halo C₁-C₆ alkylsulfonyl group, n) amono C₁-C₆ alkylamino group, o) a di C₁-C₆ alkylamino group wherein thealkyl groups are the same or different, and p) a C₁-C₆ alkoxycarbonylgroup, 72a) a C₁-C₆ alkylcarbonyloxy C₁-C₆ alkyl group, 73a) a C₁-C₆alkylcarbonyl C₁-C₆ alkylcarbonyl group, or 74a) a C₁-C₆ alkoxycarbonylC₁-C₆ alkylcarbonyl group;R² is 1b) a hydrogen atom, 2b) a halogen atom, 3b) a C₁-C₆ alkyl group,4b) a halo C₁-C₆ alkyl group, 5b) a cyano group, 6b) a hydroxy group,7b) a C₁-C₆ alkoxy group, 8b) a halo C₁-C₆ alkoxy group, 9b) a C₁-C₆alkoxy C₁-C₃ alkoxy group, 10b) a halo C₁-C₆ alkoxy C₁-C₃ alkoxy group,11b) a C₁-C₆ alkylthio C₁-C₃ alkoxy group, 12b) a halo C₁-C₆ alkylthioC₁-C₃ alkoxy group, 13b) a C₁-C₆ alkylsulfinyl C₁-C₃ alkoxy group, 14b)a halo C₁-C₆ alkylsulfinyl C₁-C₃ alkoxy group, 15b) a C₁-C₆alkylsulfonyl C₁-C₃ alkoxy group, 16b) a halo C₁-C₆ alkylsulfonyl C₁-C₃alkoxy group, 17b) a mono C₁-C₆ alkylamino C₁-C₃ alkoxy group, 18b) a diC₁-C₆ alkylamino C₁-C₃ alkoxy group wherein the alkyl groups are thesame or different, 19b) a C₁-C₆ alkylthio group, 20b) a halo C₁-C₆alkylthio group, 21b) a C₁-C₆ alkylsulfinyl group, 22b) a halo C₁-C₆alkylsulfinyl group, 23b) a C₁-C₆ alkylsulfonyl group, 24b) a halo C₁-C₆alkylsulfonyl group, 25b) an amino group, 26b) a mono C₁-C₆ alkylaminogroup, 27b) a di C₁-C₆ alkylamino group wherein the alkyl groups are thesame or different, 28b) a phenoxy group, 29b) a substituted phenoxygroup having, on the ring, one or more, the same or differentsubstituents selected from a) a halogen atom, b) a cyano group, c) anitro group, d) a C₁-C₆ alkyl group, e) a halo C₁-C₆ alkyl group, f) aC₁-C₆ alkoxy group, g) a halo C₁-C₆ alkoxy group, h) a C₁-C₆ alkylthiogroup, i) a halo C₁-C₆ alkylthio group, j) a C₁-C₆ alkylsulfinyl group,k) a halo C₁-C₆ alkylsulfinyl group, l) a C₁-C₆ alkylsulfonyl group, m)a halo C₁-C₆ alkylsulfonyl group, n) a mono C₁-C₆ alkylamino group, o) adi C₁-C₆ alkylamino group wherein the alkyl groups are the same ordifferent, and p) a C₁-C₆ alkoxycarbonyl group, 30b) a phenylthio group,31b) a substituted phenylthio group having, on the ring, one or more,the same or different substituents selected from a) a halogen atom, b) acyano group, c) a nitro group, d) a C₁-C₆ alkyl group, e) a halo C₁-C₆alkyl group, f) a C₁-C₆ alkoxy group, g) a halo C₁-C₆ alkoxy group, h) aC₁-C₆ alkylthio group, i) a halo C₁-C₆ alkylthio group, j) a C₁-C₆alkylsulfinyl group, k) a halo C₁-C₆ alkylsulfinyl group, l) a C₁-C₆alkylsulfonyl group, m) a halo C₁-C₆ alkylsulfonyl group, n) a monoC₁-C₆ alkylamino group, o) a di C₁-C₆ alkylamino group wherein the alkylgroups are the same or different, and p) a C₁-C₆ alkoxycarbonyl group,32b) a phenylsulfinyl group, 33b) a substituted phenylsulfinyl grouphaving, on the ring, one or more, the same or different substituentsselected from a) a halogen atom, b) a cyano group, c) a nitro group, d)a C₁-C₆ alkyl group, e) a halo C₁-C₆ alkyl group, f) a C₁-C₆ alkoxygroup, g) a halo C₁-C₆ alkoxy group, h) a C₁-C₆ alkylthio group, i) ahalo C₁-C₆ alkylthio group, j) a C₁-C₆ alkylsulfinyl group, k) a haloC₁-C₆ alkylsulfinyl group, l) a C₁-C₆ alkylsulfonyl group, m) a haloC₁-C₆ alkylsulfonyl group, n) a mono C₁-C₆ alkylamino group, o) a diC₁-C₆ alkylamino group wherein the alkyl groups are the same ordifferent, and p) a C₁-C₆ alkoxycarbonyl group, 34b) a phenylsulfonylgroup, 35b) a substituted phenylsulfonyl group having, on the ring, oneor more, the same or different substituents selected from a) a halogenatom, b) a cyano group, c) a nitro group, d) a C₁-C₆ alkyl group, e) ahalo C₁-C₆ alkyl group, f) a C₁-C₆ alkoxy group, g) a halo C₁-C₆ alkoxygroup, h) a C₁-C₆ alkylthio group, i) a halo C₁-C₆ alkylthio group, j) aC₁-C₆ alkylsulfinyl group, k) a halo C₁-C₆ alkylsulfinyl group, l) aC₁-C₆ alkylsulfonyl group, m) a halo C₁-C₆ alkylsulfonyl group, n) amono C₁-C₆ alkylamino group, o) a di C₁-C₆ alkylamino group wherein thealkyl groups are the same or different, and p) a C₁-C₆ alkoxycarbonylgroup, 36b) a phenyl C₁-C₆ alkoxy group, or 37b) a substituted phenylC₁-C₆ alkoxy group having, on the ring, one or more, the same ordifferent substituents selected from a) a halogen atom, b) a cyanogroup, c) a nitro group, d) a C₁-C₆ alkyl group, e) a halo C₁-C₆ alkylgroup, f) a C₁-C₆ alkoxy group, g) a halo C₁-C₆ alkoxy group, h) a C₁-C₆alkylthio group, i) a halo C₁-C₆ alkylthio group, j) a C₁-C₆alkylsulfinyl group, k) a halo C₁-C₆ alkylsulfinyl group, l) a C₁-C₆alkylsulfonyl group, m) a halo C₁-C₆ alkylsulfonyl group, n) a monoC₁-C₆ alkylamino group, o) a di C₁-C₆ alkylamino group wherein the alkylgroups are the same or different, and p) a C₁-C₆ alkoxycarbonyl group;G is 1c) a C₂-C₁₀ alkyl group, 2c) a halo C₂-C₁₀ alkyl group, 3c) aC₃-C₁₀ alkenyl group, 4c) a halo C₃-C₁₀ alkenyl group, 5c) a C₃-C₁₀alkynyl group, 6c) a halo C₃-C₁₀ alkynyl group, 7c) a C₃-C₁₀ cycloalkylgroup, 8c) a substituted C₃-C₁₀ cycloalkyl group having, on the ring,one or more, the same or different substituents selected from a) ahalogen atom, b) a C₁-C₆ alkyl group, and c) a halo C₁-C₆ alkyl group,9c) a C₃-C₁₀ cycloalkenyl group, 10c) a substituted C₃-C₁₀ cycloalkenylgroup having, on the ring, one or more, the same or differentsubstituents selected from a) a halogen atom, b) a C₁-C₆ alkyl group,and c) a halo C₁-C₆ alkyl group, 11c) a C₃-C₈ cycloalkyl C₁-C₆ alkylgroup, or 12c) a halo C₃-C₈ cycloalkyl C₁-C₆ alkyl group;Z is an oxygen atom or a sulfur atom;X may be the same or different and is 1d) a hydrogen atom, 2d) a halogenatom, 3d) a cyano group, 4d) a nitro group, 5d) a C₁-C₆ alkyl group, or6d) a halo C₁-C₆ alkyl group;Y¹ is 1e) a hydrogen atom, 2e) a C₁-C₆ alkyl group, 3e) a halo C₁-C₆alkyl group, 4e) a C₂-C₆ alkenyl group, 5e) a halo C₂-C₆ alkenyl group,6e) a C₂-C₆ alkynyl group, 7e) a halo C₂-C₆ alkynyl group, 8e) a C₁-C₆alkoxy C₁-C₆ alkoxy C₁-C₆ alkyl group, 9e) a hydroxy C₁-C₆ alkyl group,10e) a C₁-C₆ alkylcarbonyloxy C₁-C₆ alkyl group, 11e) a C₃-C₆ cycloalkylgroup, 12e) a halo C₃-C₆ cycloalkyl group, 13e) a C₃-C₆ cycloalkyl C₁-C₆alkyl group, 14e) a halo C₃-C₆ cycloalkyl C₁-C₆ alkyl group, 15e) aC₁-C₆ alkylsulfonyl group, 16e) a halo C₁-C₆ alkylsulfonyl group, 17e) aC₁-C₆ alkylthio C₁-C₆ alkyl group, 18e) a halo C₁-C₆ alkylthio C₁-C₆alkyl group, 19e) a C₁-C₆ alkylsulfinyl C₁-C₆ alkyl group, 20e) a haloC₁-C₆ alkylsulfinyl C₁-C₆ alkyl group, 21e) a C₁-C₆ alkylsulfonyl C₁-C₆alkyl group, 22e) a halo C₁-C₆ alkylsulfonyl C₁-C₆ alkyl group, 23e) amono C₁-C₆ alkylamino C₁-C₆ alkyl group, 24e) a di C₁-C₆ alkylaminoC₁-C₆ alkyl group wherein the alkyl groups are the same or different,25e) a phenyl group, 26e) a substituted phenyl group having, on thering, one or more, the same or different substituents selected from a) ahalogen atom, b) a cyano group, c) a nitro group, d) a C₁-C₆ alkylgroup, e) a halo C₁-C₆ alkyl group, f) a C₁-C₆ alkoxy group, g) a haloC₁-C₆ alkoxy group, h) a C₁-C₆ alkylthio group, i) a halo C₁-C₆alkylthio group, j) a C₁-C₆ alkylsulfinyl group, k) a halo C₁-C₆alkylsulfinyl group, l) a C₁-C₆ alkylsulfonyl group, m) a halo C₁-C₆alkylsulfonyl group, n) a mono C₁-C₆ alkylamino group, o) a di C₁-C₆alkylamino group wherein the alkyl groups are the same or different, andp) a C₁-C₆ alkoxycarbonyl group;Y² may be the same or different and is 1f) a hydrogen atom, 2f) ahalogen atom, 3f) a cyano group, 4f) a nitro group, 5f) a hydroxylgroup, 6f) a mercapto group, 7f) an amino group, 8f) a carboxyl group,9f) a C₁-C₆ alkyl group, 10f) a halo C₁-C₆ alkyl group, 11f) a C₂-C₆alkenyl group, 12f) a halo C₂-C₆ alkenyl group, 13f) a C₂-C₆ alkynylgroup, 14f) a halo C₂-C₆ alkynyl group, 15f) a tri C₁-C₆ alkylsilylC₂-C₆ alkynyl group wherein the alkyl groups are the same or different,16f) a phenyl C₂-C₆ alkynyl group, 17f) a C₁-C₆ alkoxy C₁-C₆ alkoxyC₁-C₆ alkyl group, 18f) a hydroxy C₁-C₆ alkyl group, 19f) a C₁-C₆alkylcarbonyloxy C₁-C₆ alkyl group, 20f) a C₃-C₆ cycloalkyl group, 21f)a halo C₃-C₆ cycloalkyl group, 22f) a C₃-C₆ cycloalkyl C₁-C₆ alkylgroup, 23f) a halo C₃-C₆ cycloalkyl C₁-C₆ alkyl group, 24f) a C₁-C₆alkoxy group, 25f) a halo C₁-C₆ alkoxy group, 26f) a C₁-C₆ alkoxy C₁-C₆alkoxy group, 27f) a halo C₁-C₆ alkoxy C₁-C₆ alkoxy group, 28f) a phenylC₁-C₆ alkoxy group, 29f) a C₁-C₆ alkoxy C₁-C₆ alkyl group, 30f) a haloC₁-C₆ alkoxy C₁-C₆ alkyl group, 31f) a C₁-C₆ alkylthio group, 32f) ahalo C₁-C₆ alkylthio group, 33f) a C₁-C₆ alkylsulfinyl group, 34f) ahalo C₁-C₆ alkylsulfinyl group, 35f) a C₁-C₆ alkylsulfonyl group, 36f) ahalo C₁-C₆ alkylsulfonyl group, 37f) a C₁-C₆ alkylthio C₁-C₆ alkylgroup, 38f) a halo C₁-C₆ alkylthio C₁-C₆ alkyl group, 39f) a C₁-C₆alkylsulfinyl C₁-C₆ alkyl group, 40f) a halo C₁-C₆ alkylsulfinyl C₁-C₆alkyl group, 41f) a C₁-C₆ alkylsulfonyl C₁-C₆ alkyl group, 42f) a haloC₁-C₆ alkylsulfonyl C₁-C₆ alkyl group, 43f) a mono C₁-C₆ alkylaminogroup, 44f) a di C₁-C₆ alkylamino group wherein the alkyl groups are thesame or different, 45f) a phenylamino group, 46f) a mono C₁-C₆alkylamino C₁-C₆ alkyl group, 47f) a di C₁-C₆ alkylamino C₁-C₆ alkylgroup wherein the alkyl groups are the same or different, 48f) a phenylgroup, 49f) a substituted phenyl group having, on the ring, one or more,the same or different substituents selected from a) a halogen atom, b) acyano group, c) a nitro group, d) a C₁-C₆ alkyl group, e) a halo C₁-C₆alkyl group, f) a C₁-C₆ alkoxy group, g) a halo C₁-C₆ alkoxy group, h) aC₁-C₆ alkylthio group, i) a halo C₁-C₆ alkylthio group, j) a C₁-C₆alkylsulfinyl group, k) a halo C₁-C₆ alkylsulfinyl group, l) a C₁-C₆alkylsulfonyl group, m) a halo C₁-C₆ alkylsulfonyl group, n) a monoC₁-C₆ alkylamino group, o) a di C₁-C₆ alkylamino group wherein the alkylgroups are the same or different, and p) a C₁-C₆ alkoxycarbonyl group,50f) a phenoxy group, 51f) a substituted phenoxy group having, on thering, one or more, the same or different substituents selected from a) ahalogen atom, b) a cyano group, c) a nitro group, d) a C₁-C₆ alkylgroup, e) a halo C₁-C₆ alkyl group, f) a C₁-C₆ alkoxy group, g) a haloC₁-C₆ alkoxy group, h) a C₁-C₆ alkylthio group, i) a halo C₁-C₆alkylthio group, j) a C₁-C₆ alkylsulfinyl group, k) a halo C₁-C₆alkylsulfinyl group, l) a C₁-C₆ alkylsulfonyl group, m) a halo C₁-C₆alkylsulfonyl group, n) a mono C₁-C₆ alkylamino group, o) a di C₁-C₆alkylamino group wherein the alkyl groups are the same or different, andp) a C₁-C₆ alkoxycarbonyl group, 52f) a heterocyclic group, or 53f) asubstituted heterocyclic group having, on the ring, one or more, thesame or different substituents selected from a) a halogen atom, b) acyano group, c) a nitro group, d) a C₁-C₆ alkyl group, e) a halo C₁-C₆alkyl group, f) a C₁-C₆ alkoxy group, g) a halo C₁-C₆ alkoxy group, h) aC₁-C₆ alkylthio group, i) a halo C₁-C₆ alkylthio group, j) a C₁-C₆alkylsulfinyl group, k) a halo C₁-C₆ alkylsulfinyl group, l) a C₁-C₆alkylsulfonyl group, m) a halo C₁-C₆ alkylsulfonyl group, n) a monoC₁-C₆ alkylamino group, o) a di C₁-C₆ alkylamino group wherein the alkylgroups are the same or different, and p) a C₁-C₆ alkoxycarbonyl group;m is 1 or 2; andn is an integer of 1-3,salts thereof and agrohorticultural agents containing the compound as anactive ingredient, and methods of use thereof.

In addition, the present invention also relates to substituted anilinederivatives represented by the formula (II), which are intermediatestherefor:

whereinR¹ is 1a) a hydrogen atom, 2a) a C₁-C₈ alkyl group, 3a) a halo C₁-C₆alkyl group, 4a) a C₁-C₆ alkylcarbonyl group, 5a) a halo C₁-C₆alkylcarbonyl group, 6a) a C₂-C₆ alkenylcarbonyl group, 7a) a halo C₂-C₆alkenylcarbonyl group, 8a) a C₁-C₆ alkylcarbonyl C₁-C₆ alkyl group, 9a)a C₃-C₆ cycloalkyl group, 10a) a halo C₃-C₆ cycloalkyl group, 11a) aC₃-C₆ cycloalkyl C₁-C₆ alkyl group, 12a) a halo C₃-C₆ cycloalkyl C₁-C₆alkyl group, 13a) a C₂-C₆ alkenyl group, 14a) a halo C₂-C₆ alkenylgroup, 15a) a C₂-C₆ alkynyl group, 16a) a halo C₂-C₆ alkynyl group, 17a)a C₁-C₁₀ alkoxy C₁-C₆ alkyl group, 18a) a halo C₁-C₆ alkoxy C₁-C₆ alkylgroup, 19a) a C₂-C₆ alkenyloxy C₁-C₆ alkyl group, 20a) a C₁-C₆ alkoxyC₁-C₆ alkoxy C₁-C₆ alkyl group, 21a) a C₁-C₆ alkylthio C₁-C₆ alkylgroup, 22a) a halo C₁-C₆ alkylthio C₁-C₆ alkyl group, 23a) a C₁-C₆alkylsulfinyl C₁-C₆ alkyl group, 24a) a halo C₁-C₆ alkylsulfinyl C₁-C₆alkyl group, 25a) a C₁-C₆ alkylsulfonyl C₁-C₆ alkyl group, 26a) a haloC₁-C₆ alkylsulfonyl C₁-C₆ alkyl group, 27a) a mono C₁-C₆ alkylaminoC₁-C₆ alkyl group, 28a) a di C₁-C₆ alkylamino C₁-C₆ alkyl group whereinthe alkyl groups are the same or different, 29a) a phenyl C₁-C₆ alkoxyC₁-C₆ alkyl group, 30a) a substituted phenyl C₁-C₆ alkoxy C₁-C₆ alkylgroup having, on the ring, one or more, the same or differentsubstituents selected from a) a halogen atom, b) a cyano group, c) anitro group, d) a C₁-C₆ alkyl group, e) a halo C₁-C₆ alkyl group, f) aC₁-C₆ alkoxy group, g) a halo C₁-C₆ alkoxy group, h) a C₁-C₆ alkylthiogroup, i) a halo C₁-C₆ alkylthio group, j) a C₁-C₆ alkylsulfinyl group,k) a halo C₁-C₆ alkylsulfinyl group, l) a C₁-C₆ alkylsulfonyl group, m)a halo C₁-C₆ alkylsulfonyl group, n) a mono C₁-C₆ alkylamino group, o) adi C₁-C₆ alkylamino group wherein the alkyl groups are the same ordifferent, and p) a C₁-C₆ alkoxycarbonyl group, 31a) a C₁-C₁₆alkoxycarbonyl group, 32a) a C₁-C₆ alkoxy C₁-C₆ alkoxycarbonyl group,33a) a halo C₁-C₆ alkoxycarbonyl group, 34a) a C₂-C₆ alkenyloxycarbonylgroup, 35a) a C₁-C₆ alkylthiocarbonyl group, 36a) a mono C₁-C₆alkylaminocarbonyl group, 37a) a di C₁-C₆ alkylaminocarbonyl groupwherein the alkyl groups are the same or different, 38a) a C₁-C₆alkoxycarbonyl C₁-C₆ alkyl group, 39a) a C₁-C₆ alkylsulfonyl group, 40a)a halo C₁-C₆ alkylsulfonyl group, 41a) a cyano C₁-C₆ alkyl group, 42a) aphenyl C₁-C₆ alkyl group, 43a) a substituted phenyl C₁-C₆ alkyl grouphaving, on the ring, one or more, the same or different substituentsselected from a) a halogen atom, b) a cyano group, c) a nitro group, d)a C₁-C₆ alkyl group, e) a halo C₁-C₆ alkyl group, f) a C₁-C₆ alkoxygroup, g) a halo C₁-C₆ alkoxy group, h) a C₁-C₆ alkylthio group, i) ahalo C₁-C₆ alkylthio group, j) a C₁-C₆ alkylsulfinyl group, k) a haloC₁-C₆ alkylsulfinyl group, l) a C₁-C₆ alkylsulfonyl group, m) a haloC₁-C₆ alkylsulfonyl group, n) a mono C₁-C₆ alkylamino group, o) a diC₁-C₆ alkylamino group wherein the alkyl groups are the same ordifferent, and p) a C₁-C₆ alkoxycarbonyl group, 44a) a phenylcarbonylgroup, 45a) a substituted phenylcarbonyl group having, on the ring, oneor more, the same or different substituents selected from a) a halogenatom, b) a cyano group, c) a nitro group, d) a C₁-C₆ alkyl group, e) ahalo C₁-C₆ alkyl group, f) a C₁-C₆ alkoxy group, g) a halo C₁-C₆ alkoxygroup, h) a C₁-C₆ alkylthio group, i) a halo C₁-C₆ alkylthio group, j) aC₁-C₆ alkylsulfinyl group, k) a halo C₁-C₆ alkylsulfinyl group, l) aC₁-C₆ alkylsulfonyl group, m) a halo C₁-C₆ alkylsulfonyl group, n) amono C₁-C₆ alkylamino group, o) a di C₁-C₆ alkylamino group wherein thealkyl groups are the same or different, and p) a C₁-C₆ alkoxycarbonylgroup, 46a) a heterocyclylcarbonyl group, 47a) a substitutedheterocyclylcarbonyl group having, on the ring, one or more, the same ordifferent substituents selected from a) a halogen atom, b) a cyanogroup, c) a nitro group, d) a C₁-C₆ alkyl group, e) a halo C₁-C₆ alkylgroup, f) a C₁-C₆ alkoxy group, g) a halo C₁-C₆ alkoxy group, h) a C₁-C₆alkylthio group, i) a halo C₁-C₆ alkylthio group, j) a C₁-C₆alkylsulfinyl group, k) a halo C₁-C₆ alkylsulfinyl group, l) a C₁-C₆alkylsulfonyl group, m) a halo C₁-C₆ alkylsulfonyl group, n) a monoC₁-C₆ alkylamino group, o) a di C₁-C₆ alkylamino group wherein the alkylgroups are the same or different, and p) a C₁-C₆ alkoxycarbonyl group,48a) a phenoxycarbonyl group, 49a) a substituted phenoxycarbonyl grouphaving, on the ring, one or more, the same or different substituentsselected from a) a halogen atom, b) a cyano group, c) a nitro group, d)a C₁-C₆ alkyl group, e) a halo C₁-C₆ alkyl group, f) a C₁-C₆ alkoxygroup, g) a halo C₁-C₆ alkoxy group, h) a C₁-C₆ alkylthio group, i) ahalo C₁-C₆ alkylthio group, j) a C₁-C₆ alkylsulfinyl group, k) a haloC₁-C₆ alkylsulfinyl group, l) a C₁-C₆ alkylsulfonyl group, m) a haloC₁-C₆ alkylsulfonyl group, n) a mono C₁-C₆ alkylamino group, o) a diC₁-C₆ alkylamino group wherein the alkyl groups are the same ordifferent, and p) a C₁-C₆ alkoxycarbonyl group, 50a) a phenoxy C₁-C₆alkylcarbonyl group, 51a) a substituted phenoxy C₁-C₆ alkylcarbonylgroup having, on the ring, one or more, the same or differentsubstituents selected from a) a halogen atom, b) a cyano group, c) anitro group, d) a C₁-C₆ alkyl group, e) a halo C₁-C₆ alkyl group, f) aC₁-C₆ alkoxy group, g) a halo C₁-C₆ alkoxy group, h) a C₁-C₆ alkylthiogroup, i) a halo C₁-C₆ alkylthio group, j) a C₁-C₆ alkylsulfinyl group,k) a halo C₁-C₆ alkylsulfinyl group, l) a C₁-C₆ alkylsulfonyl group, m)a halo C₁-C₆ alkylsulfonyl group, n) a mono C₁-C₆ alkylamino group, o) adi C₁-C₆ alkylamino group wherein the alkyl groups are the same ordifferent, and p) a C₁-C₆ alkoxycarbonyl group, 52a) a phenylsulfonylgroup, 53a) a substituted phenylsulfonyl group having, on the ring, oneor more, the same or different substituents selected from a) a halogenatom, b) a cyano group, c) a nitro group, d) a C₁-C₆ alkyl group, e) ahalo C₁-C₆ alkyl group, f) a C₁-C₆ alkoxy group, g) a halo C₁-C₆ alkoxygroup, h) a C₁-C₆ alkylthio group, i) a halo C₁-C₆ alkylthio group, j) aC₁-C₆ alkylsulfinyl group, k) a halo C₁-C₆ alkylsulfinyl group, l) aC₁-C₆ alkylsulfonyl group, m) a halo C₁-C₆ alkylsulfonyl group, n) amono C₁-C₆ alkylamino group, o) a di C₁-C₆ alkylamino group wherein thealkyl groups are the same or different, and p) a C₁-C₆ alkoxycarbonylgroup, 54a) a di C₁-C₆ alkylphosphono group wherein the alkyl groups arethe same or different, 55a) a di C₁-C₆ alkylphosphonothio group whereinthe alkyl groups are the same or different, 56a) a N—C₁-C₆ alkyl-N—C₁-C₆alkoxycarbonylaminothio group, 57a) a N—C₁-C₆ alkyl-N—C₁-C₆alkoxycarbonyl C₁-C₆ alkylaminothio group, 58a) a di C₁-C₆alkylaminothio group wherein the alkyl groups are the same or different,59a) a C₃-C₆ cycloalkylcarbonyl group, 60a) a halo C₃-C₆cycloalkylcarbonyl group, 61a) a C₁-C₆ alkyl C₃-C₆ cycloalkylcarbonylgroup, 62a) a halo C₁-C₆ alkyl C₃-C₆ cycloalkylcarbonyl group, 63a) aphenyl C₁-C₆ alkylcarbonyl group, 64a) a substituted phenyl C₁-C₆alkylcarbonyl group having, on the ring, one or more, the same ordifferent substituents selected from a) a halogen atom, b) a cyanogroup, c) a nitro group, d) a C₁-C₆ alkyl group, e) a halo C₁-C₆ alkylgroup, f) a C₁-C₆ alkoxy group, g) a halo C₁-C₆ alkoxy group, h) a C₁-C₆alkylthio group, i) a halo C₁-C₆ alkylthio group, j) a C₁-C₆alkylsulfinyl group, k) a halo C₁-C₆ alkylsulfinyl group, l) a C₁-C₆alkylsulfonyl group, m) a halo C₁-C₆ alkylsulfonyl group, n) a monoC₁-C₆ alkylamino group, o) a di C₁-C₆ alkylamino group wherein the alkylgroups are the same or different, and p) a C₁-C₆ alkoxycarbonyl group,65a) a phenyl C₃-C₆ cycloalkylcarbonyl group, 66a) a substituted phenylC₃-C₆ cycloalkylcarbonyl group having, on the ring, one or more, thesame or different substituents selected from a) a halogen atom, b) acyano group, c) a nitro group, d) a C₁-C₆ alkyl group, e) a halo C₁-C₆alkyl group, f) a C₁-C₆ alkoxy group, g) a halo C₁-C₆ alkoxy group, h) aC₁-C₆ alkylthio group, i) a halo C₁-C₆ alkylthio group, j) a C₁-C₆alkylsulfinyl group, k) a halo C₁-C₆ alkylsulfinyl group, l) a C₁-C₆alkylsulfonyl group, m) a halo C₁-C₆ alkylsulfonyl group, n) a monoC₁-C₆ alkylamino group, o) a di C₁-C₆ alkylamino group wherein the alkylgroups are the same or different, and p) a C₁-C₆ alkoxycarbonyl group,67a) a C₃-C₆ cycloalkyl C₁-C₆ alkylcarbonyl group, 68a) a C₁-C₆ alkoxyC₁-C₆ alkylcarbonyl group, 69a) a halo C₃-C₆ cycloalkyl C₁-C₆alkylcarbonyl group, 70a) a phenoxy C₁-C₆ alkoxycarbonyl group, 71a) asubstituted phenoxy C₁-C₆ alkoxycarbonyl group having, on the ring, oneor more, the same or different substituents selected from a) a halogenatom, b) a cyano group, c) a nitro group, d) a C₁-C₆ alkyl group, e) ahalo C₁-C₆ alkyl group, f) a C₁-C₆ alkoxy group, g) a halo C₁-C₆ alkoxygroup, h) a C₁-C₆ alkylthio group, i) a halo C₁-C₆ alkylthio group, j) aC₁-C₆ alkylsulfinyl group, k) a halo C₁-C₆ alkylsulfinyl group, l) aC₁-C₆ alkylsulfonyl group, m) a halo C₁-C₆ alkylsulfonyl group, n) amono C₁-C₆ alkylamino group, o) a di C₁-C₆ alkylamino group wherein thealkyl groups are the same or different, and p) a C₁-C₆ alkoxycarbonylgroup, 72a) a C₁-C₆ alkylcarbonyloxy C₁-C₆ alkyl group, 73a) a C₁-C₆alkylcarbonyl C₁-C₆ alkylcarbonyl group, or 74a) a C₁-C₆ alkoxycarbonylC₁-C₆ alkylcarbonyl group;R² is 1b) a hydrogen atom, 2b) a halogen atom, 3b) a C₁-C₆ alkyl group,4b) a halo C₁-C₆ alkyl group, 5b) a cyano group, 6b) a hydroxy group,7b) a C₁-C₆ alkoxy group, 8b) a halo C₁-C₆ alkoxy group, 9b) a C₁-C₆alkoxy C₁-C₃ alkoxy group, 10b) a halo C₁-C₆ alkoxy C₁-C₃ alkoxy group,11b) a C₁-C₆ alkylthio C₁-C₃ alkoxy group, 12b) a halo C₁-C₆ alkylthioC₁-C₃ alkoxy group, 13b) a C₁-C₆ alkylsulfinyl C₁-C₃ alkoxy group, 14b)a halo C₁-C₆ alkylsulfinyl C₁-C₃ alkoxy group, 15b) a C₁-C₆alkylsulfonyl C₁-C₃ alkoxy group, 16b) a halo C₁-C₆ alkylsulfonyl C₁-C₃alkoxy group, 17b) a mono C₁-C₆ alkylamino C₁-C₃ alkoxy group, 18b) a diC₁-C₆ alkylamino C₁-C₃ alkoxy group wherein the alkyl groups are thesame or different, 19b) a C₁-C₆ alkylthio group, 20b) a halo C₁-C₆alkylthio group, 21b) a C₁-C₆ alkylsulfinyl group, 22b) a halo C₁-C₆alkylsulfinyl group, 23b) a C₁-C₆ alkylsulfonyl group, 24b) a halo C₁-C₆alkylsulfonyl group, 25b) an amino group, 26b) a mono C₁-C₆ alkylaminogroup, 27b) a di C₁-C₆ alkylamino group wherein the alkyl groups are thesame or different, 28b) a phenoxy group, 29b) a substituted phenoxygroup having, on the ring, one or more, the same or differentsubstituents selected from a) a halogen atom, b) a cyano group, c) anitro group, d) a C₁-C₆ alkyl group, e) a halo C₁-C₆ alkyl group, f) aC₁-C₆ alkoxy group, g) a halo C₁-C₆ alkoxy group, h) a C₁-C₆ alkylthiogroup, i) a halo C₁-C₆ alkylthio group, j) a C₁-C₆ alkylsulfinyl group,k) a halo C₁-C₆ alkylsulfinyl group, l) a C₁-C₆ alkylsulfonyl group, m)a halo C₁-C₆ alkylsulfonyl group, n) a mono C₁-C₆ alkylamino group, o) adi C₁-C₆ alkylamino group wherein the alkyl groups are the same ordifferent, and p) a C₁-C₆ alkoxycarbonyl group, 30b) a phenylthio group,31b) a substituted phenylthio group having, on the ring, one or more,the same or different substituents selected from a) a halogen atom, b) acyano group, c) a nitro group, d) a C₁-C₆ alkyl group, e) a halo C₁-C₆alkyl group, f) a C₁-C₆ alkoxy group, g) a halo C₁-C₆ alkoxy group, h) aC₁-C₆ alkylthio group, i) a halo C₁-C₆ alkylthio group, j) a C₁-C₆alkylsulfinyl group, k) a halo C₁-C₆ alkylsulfinyl group, l) a C₁-C₆alkylsulfonyl group, m) a halo C₁-C₆ alkylsulfonyl group, n) a monoC₁-C₆ alkylamino group, o) a di C₁-C₆ alkylamino group wherein the alkylgroups are the same or different, and p) a C₁-C₆ alkoxycarbonyl group,32b) a phenylsulfinyl group, 33b) a substituted phenylsulfinyl grouphaving, on the ring, one or more, the same or different substituentsselected from a) a halogen atom, b) a cyano group, c) a nitro group, d)a C₁-C₆ alkyl group, e) a halo C₁-C₆ alkyl group, f) a C₁-C₆ alkoxygroup, g) a halo C₁-C₆ alkoxy group, h) a C₁-C₆ alkylthio group, i) ahalo C₁-C₆ alkylthio group, j) a C₁-C₆ alkylsulfinyl group, k) a haloC₁-C₆ alkylsulfinyl group, l) a C₁-C₆ alkylsulfonyl group, m) a haloC₁-C₆ alkylsulfonyl group, n) a mono C₁-C₆ alkylamino group, o) a diC₁-C₆ alkylamino group wherein the alkyl groups are the same ordifferent, and p) a C₁-C₆ alkoxycarbonyl group, 34b) a phenylsulfonylgroup, 35b) a substituted phenylsulfonyl group having, on the ring, oneor more, the same or different substituents selected from a) a halogenatom, b) a cyano group, c) a nitro group, d) a C₁-C₆ alkyl group, e) ahalo C₁-C₆ alkyl group, f) a C₁-C₆ alkoxy group, g) a halo C₁-C₆ alkoxygroup, h) a C₁-C₆ alkylthio group, i) a halo C₁-C₆ alkylthio group, j) aC₁-C₆ alkylsulfinyl group, k) a halo C₁-C₆ alkylsulfinyl group, l) aC₁-C₆ alkylsulfonyl group, m) a halo C₁-C₆ alkylsulfonyl group, n) amono C₁-C₆ alkylamino group, o) a di C₁-C₆ alkylamino group wherein thealkyl groups are the same or different, and p) a C₁-C₆ alkoxycarbonylgroup, 36b) a phenyl C₁-C₆ alkoxy group, or 37b) a substituted phenylC₁-C₆ alkoxy group having, on the ring, one or more, the same ordifferent substituents selected from a) a halogen atom, b) a cyanogroup, c) a nitro group, d) a C₁-C₆ alkyl group, e) a halo C₁-C₆ alkylgroup, f) a C₁-C₆ alkoxy group, g) a halo C₁-C₆ alkoxy group, h) a C₁-C₆alkylthio group, i) a halo C₁-C₆ alkylthio group, j) a C₁-C₆alkylsulfinyl group, k) a halo C₁-C₆ alkylsulfinyl group, l) a C₁-C₆alkylsulfonyl group, m) a halo C₁-C₆ alkylsulfonyl group, n) a monoC₁-C₆ alkylamino group, o) a di C₁-C₆ alkylamino group wherein the alkylgroups are the same or different, and p) a C₁-C₆ alkoxycarbonyl group;G is 1c) a C₂-C₁₀ alkyl group, 2c) a halo C₂-C₁₀ alkyl group, 3c) aC₃-C₁₀ alkenyl group, 4c) a halo C₃-C₁₀ alkenyl group, 5c) a C₃-C₁₀alkynyl group, 6c) a halo C₃-C₁₀ alkynyl group, 7c) a C₃-C₁₀ cycloalkylgroup, 8c) a substituted C₃-C₁₀ cycloalkyl group having, on the ring,one or more, the same or different substituents selected from a) ahalogen atom, b) a C₁-C₆ alkyl group, and c) a halo C₁-C₆ alkyl group,9c) a C₃-C₁₀ cycloalkenyl group, 10c) a substituted C₃-C₁₀ cycloalkenylgroup having, on the ring, one or more, the same or differentsubstituents selected from a) a halogen atom, b) a C₁-C₆ alkyl group,and c) a halo C₁-C₆ alkyl group, 11c) a C₃-C₈ cycloalkyl C₁-C₆ alkylgroup, or 12c) a halo C₃-C₈ cycloalkyl C₁-C₆ alkyl group;X may be the same or different and is 1d) a hydrogen atom, 2d) a halogenatom, 3d) a cyano group, 4d) a nitro group, 5d) a C₁-C₆ alkyl group, or6d) a halo C₁-C₆ alkyl group;n is an integer of 1-3,salts thereof and 1,3-dimethyl-5-trifluoromethylpyrazole-4-carboxylicacid and a salt thereof.

BEST MODE FOR EMBODYING THE INVENTION

In the definitions of a substituted pyrazolecarboxanilide derivative ofthe formula (I) and a substituted aniline derivative of the formula (II)of the present invention, “halo”, “C₁-C₆ alkyl”, “C₁-C₆ alkoxyl”, “C₂-C₆alkenyl”, “C₂-C₆ alkynyl” or “a heterocyclic group”, and the like ineach of substituents has the following meaning.

The “halo” or “halogen atom” means a chlorine atom, a bromine atom, aniodine atom or a fluorine atom.

The “C₁-C₆ alkyl” is linear or branched chain alkyl having 1 to 6 carbonatoms, such as methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl,s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl,2-methylbutyl, 1-ethylpropyl, n-hexyl, 2-ethylbutyl and the like.

The “C₁-C₈ alkyl” is linear or branched chain alkyl having 1 to 8 carbonatoms, such as methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl,s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl,2-methylbutyl, 1-ethylpropyl, n-hexyl, 2-ethylbutyl, n-heptyl, n-octyl,2-ethylhexyl and the like.

The “C₂-C₁₀ alkyl” is linear or branched chain alkyl having 2 to 10carbon atoms, such as ethyl, n-propyl, i-propyl, n-butyl, i-butyl,s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl,2-methylbutyl, n-hexyl, 2-ethylbutyl, 1-ethylpropyl, n-heptyl, n-octyl,2-ethylhexyl, n-nonyl, n-decyl and the like.

The “C₃-C₆ cycloalkyl” is cyclic alkyl having 3 to 6 carbon atoms, suchas cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like.

The “C₃-C₈ cycloalkyl” is cyclic alkyl having 3 to 8 carbon atoms, suchas cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclooctyl and thelike.

The “C₃-C₁₀ cycloalkyl” is cyclic alkyl having 3 to 10 carbon atoms,such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclooctyl,cyclodecyl and the like.

The “C₃-C₁₀ cycloalkenyl” is cyclic alkenyl having 3 to 10 carbon atoms,such as cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl,cyclooctenyl, cyclodecenyl and the like.

The “C₁-C₃ alkoxy” is alkoxy wherein its alkyl moiety is linear orbranched chain alkyl having 1 to 3 carbon atoms, such as methoxy,ethoxy, propoxy, isopropoxy and the like.

The “C₁-C₆ alkoxy” is alkoxy wherein its alkyl moiety is theabove-mentioned “C₁-C₆ alkyl”, such as methoxy, ethoxy, n-propoxy,i-propoxy, n-butoxy, isobutoxy, s-butoxy, t-butoxy, n-pentyloxy,isopentyloxy, neopentyloxy, t-pentyloxy, 2-methylbutoxy, 1-ethylpropoxy,hexyloxy, 2-ethylbutoxy and the like.

The “C₁-C₁₀ alkoxy” is alkoxy wherein its alkyl moiety is linear orbranched chain alkyl having 1 to 10 carbon atoms, such as methoxy,ethoxy, n-propoxy, i-propoxy, n-butoxy, isobutoxy, s-butoxy, t-butoxy,n-pentyloxy, isopentyloxy, neopentyloxy, t-pentyloxy, 2-methylbutoxy,1-ethylpropoxy, hexyloxy, 2-ethylbutoxy, n-heptyloxy, n-octyloxy,2-ethylhexyloxy, n-nonyloxy, n-decyloxy and the like.

The “C₁-C₁₆ alkoxy” is alkoxy wherein its alkyl moiety is linear orbranched chain alkyl having 1 to 16 carbon atoms, such as methoxy,ethoxy, n-propoxy, i-propoxy, n-butoxy, isobutoxy, s-butoxy, t-butoxy,n-pentyloxy, isopentyloxy, neopentyloxy, t-pentyloxy, 2-methylbutoxy,1-ethylpropoxy, hexyloxy, 2-ethylbutoxy, n-heptyloxy, n-octyloxy,2-ethylhexyloxy, n-nonyloxy, n-decyloxy, n-undecyloxy, n-dodecyloxy,n-tridecyloxy, n-tetradecyloxy, n-pentadecyloxy, n-hexadecyloxy and thelike.

The “C₂-C₆ alkenyl” is linear or branched chain alkenyl having 2 to 6carbon atoms, which has at least one double bond, such as vinyl,1-propenyl, allyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-pentenyl,2-methyl-1-propenyl, 2,4-pentadienyl, 3-hexenyl and the like.

The “C₃-C₁₀ alkenyl” is linear or branched chain alkenyl having 3 to 10carbon atoms, which has at least one double bond, such as 1-butenyl,2-butenyl, 3-butenyl, 2-pentenyl, 2,4-pentadienyl, 3-hexenyl,3-heptenyl, 3-octenyl, 3-nonenyl, 3-decenyl and the like.

The “C₂-C₆ alkynyl” is linear or branched chain alkynyl having 2 to 6carbon atoms, which has at least one triple bond, such as ethynyl,2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 2-pentynyl, 3-hexynyl andthe like.

The “C₃-C₁₀ alkynyl” is linear or branched chain alkynyl having 3 to 10carbon atoms, which has at least one triple bond, such as 1-butynyl,2-butynyl, 3-butynyl, 2-pentynyl, 3-hexynyl, 3-heptynyl, 3-octynyl,3-nonynyl, 3-decynyl and the like.

The numbers in “C₂-C₆”, “C₃-C₁₀” and the like shows the range of carbonatom numbers such as 2 to 6 carbon atoms and 3 to 10 carbon atoms.

Moreover, the above-mentioned definitions can apply to groups whereinthe above-mentioned substituents are connected. For example, “halo C₁-C₆alkyl” means linear or branched chain alkyl group having 1 to 6 carbonatoms, which is substituted by the same or different one or more halogenatoms, such as chloromethyl, 2-chloroethyl, 2,2,2-trichloroethyl,3-chloropropyl, 2-chloro-1,1-dimethylethyl, 1-bromo-1-methylethyl,difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, perfluorohexyland the like.

“A heterocyclic group” and “A heterocyclyl” are 5- or 6-memberedheterocyclic groups having one or more hetero atoms selected from anoxygen atom, a sulfur atom and a nitrogen atom including, for example,pyridyl group, pyridine-N-oxide group, pyrimidinyl group, furyl group,tetrahydrofuryl group, thienyl group, tetrahydrothienyl group,tetrahydropyranyl group, tetrahydrothiopyranyl group, oxazolyl group,isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolylgroup, thiadiazolyl group, imidazolyl group, triazolyl group andpyrazolyl group.

A salt of a substituted pyrazolecarboxanilide derivative represented bythe formula (I) of the present invention includes a salt of an alkalimetal (lithium, sodium, potassium, etc.); a salt of an alkaline earthmetal (calcium, magnesium, etc.); an ammonium salt; and a salt of anorganic amine (methylamine, triethylamine, diethanolamine, piperidine,pyridine, etc.), or an acid addition salt. The acid addition saltincludes, for example, a carboxylate such as acetate, propionate,oxalate, trifluoroacetate, benzoate and the like; a sulfonate such asmethanesulfonate, trifluoromethanesulfonate, p-toluenesulfonate and thelike; an inorganic acid salt such as a hydrochloride, a sulfate, anitrate, a carbonate and the like.

In the substituted pyrazolecarboxanilide derivatives represented by theformula (I) of the present invention, R¹ is preferably 1a) a hydrogenatom, 2a) a C₁-C₆ alkyl group, 3a) a halo C₁-C₆ alkyl group, 4a) a C₁-C₆alkylcarbonyl group, 5a) a halo C₁-C₆ alkylcarbonyl group, 6a) a C₂-C₆alkenylcarbonyl group, 13a) a C₂-C₆ alkenyl group, 17a) a C₁-C₁₀ alkoxyC₁-C₆ alkyl group, 18a) a halo C₁-C₆ alkoxy C₁-C₆ alkyl group, 19a) aC₂-C₆ alkenyloxy C₁-C₆ alkyl group, 20a) a C₁-C₆ alkoxy C₁-C₆ alkoxyC₁-C₆ alkyl group, 29a) a phenyl C₁-C₆ alkoxy C₁-C₆ alkyl group, 30a) asubstituted phenyl C₁-C₆ alkoxy C₁-C₆ alkyl group having, on the ring,one or more, the same or different substituents selected from a) ahalogen atom, b) a cyano group, c) a nitro group, d) a C₁-C₆ alkylgroup, e) a halo C₁-C₆ alkyl group, f) a C₁-C₆ alkoxy group, g) a haloC₁-C₆ alkoxy group, h) a C₁-C₆ alkylthio group, i) a halo C₁-C₆alkylthio group, j) a C₁-C₆ alkylsulfinyl group, k) a halo C₁-C₆alkylsulfinyl group, l) a C₁-C₆ alkylsulfonyl group, m) a halo C₁-C₆alkylsulfonyl group, n) a mono C₁-C₆ alkylamino group, o) a di C₁-C₆alkylamino group wherein the alkyl groups are the same or different, andp) a C₁-C₆ alkoxycarbonyl group, 31a) a C₁-C₁₆ alkoxycarbonyl group,32a) a C₁-C₆ alkoxy C₁-C₆ alkoxycarbonyl group, 33a) a halo C₁-C₆alkoxycarbonyl group, 34a) a C₂-C₆ alkenyloxycarbonyl group, 35a) aC₁-C₆ alkylthiocarbonyl group, 42a) a phenyl C₁-C₆ alkyl group, 43a) asubstituted phenyl C₁-C₆ alkyl group having, on the ring, one or more,the same or different substituents selected from a) a halogen atom, b) acyano group, c) a nitro group, d) a C₁-C₆ alkyl group, e) a halo C₁-C₆alkyl group, f) a C₁-C₆ alkoxy group, g) a halo C₁-C₆ alkoxy group, h) aC₁-C₆ alkylthio group, i) a halo C₁-C₆ alkylthio group, j) a C₁-C₆alkylsulfinyl group, k) a halo C₁-C₆ alkylsulfinyl group, l) a C₁-C₆alkylsulfonyl group, m) a halo C₁-C₆ alkylsulfonyl group, n) a monoC₁-C₆ alkylamino group, o) a di C₁-C₆ alkylamino group wherein the alkylgroups are the same or different, and p) a C₁-C₆ alkoxycarbonyl group,44a) a phenylcarbonyl group, 45a) a substituted phenylcarbonyl grouphaving, on the ring, one or more, the same or different substituentsselected from a) a halogen atom, b) a cyano group, c) a nitro group, d)a C₁-C₆ alkyl group, e) a halo C₁-C₆ alkyl group, f) a C₁-C₆ alkoxygroup, g) a halo C₁-C₆ alkoxy group, h) a C₁-C₆ alkylthio group, i) ahalo C₁-C₆ alkylthio group, j) a C₁-C₆ alkylsulfinyl group, k) a haloC₁-C₆ alkylsulfinyl group, l) a C₁-C₆ alkylsulfonyl group, m) a haloC₁-C₆ alkylsulfonyl group, n) a mono C₁-C₆ alkylamino group, o) a diC₁-C₆ alkylamino group wherein the alkyl groups are the same ordifferent, and p) a C₁-C₆ alkoxycarbonyl group, 46a) aheterocyclylcarbonyl group, 47a) a substituted heterocyclylcarbonylgroup having, on the ring, one or more, the same or differentsubstituents selected from a) a halogen atom, b) a cyano group, c) anitro group, d) a C₁-C₆ alkyl group, e) a halo C₁-C₆ alkyl group, f) aC₁-C₆ alkoxy group, g) a halo C₁-C₆ alkoxy group, h) a C₁-C₆ alkylthiogroup, i) a halo C₁-C₆ alkylthio group, j) a C₁-C₆ alkylsulfinyl group,k) a halo C₁-C₆ alkylsulfinyl group, l) a C₁-C₆ alkylsulfonyl group, m)a halo C₁-C₆ alkylsulfonyl group, n) a mono C₁-C₆ alkylamino group, o) adi C₁-C₆ alkylamino group wherein the alkyl groups are the same ordifferent, and p) a C₁-C₆ alkoxycarbonyl group, 48a) a phenoxycarbonylgroup, 49a) a substituted phenoxycarbonyl group having, on the ring, oneor more, the same or different substituents selected from a) a halogenatom, b) a cyano group, c) a nitro group, d) a C₁-C₆ alkyl group, e) ahalo C₁-C₆ alkyl group, f) a C₁-C₆ alkoxy group, g) a halo C₁-C₆ alkoxygroup, h) a C₁-C₆ alkylthio group, i) a halo C₁-C₆ alkylthio group, j) aC₁-C₆ alkylsulfinyl group, k) a halo C₁-C₆ alkylsulfinyl group, l) aC₁-C₆ alkylsulfonyl group, m) a halo C₁-C₆ alkylsulfonyl group, n) amono C₁-C₆ alkylamino group, o) a di C₁-C₆ alkylamino group wherein thealkyl groups are the same or different, and p) a C₁-C₆ alkoxycarbonylgroup, 50a) a phenoxy C₁-C₆ alkylcarbonyl group, 51a) a substitutedphenoxy C₁-C₆ alkylcarbonyl group having, on the ring, one or more, thesame or different substituents selected from a) a halogen atom, b) acyano group, c) a nitro group, d) a C₁-C₆ alkyl group, e) a halo C₁-C₆alkyl group, f) a C₁-C₆ alkoxy group, g) a halo C₁-C₆ alkoxy group, h) aC₁-C₆ alkylthio group, i) a halo C₁-C₆ alkylthio group, j) a C₁-C₆alkylsulfinyl group, k) a halo C₁-C₆ alkylsulfinyl group, l) a C₁-C₆alkylsulfonyl group, m) a halo C₁-C₆ alkylsulfonyl group, n) a monoC₁-C₆ alkylamino group, o) a di C₁-C₆ alkylamino group wherein the alkylgroups are the same or different, and p) a C₁-C₆ alkoxycarbonyl group,52a) a phenylsulfonyl group, 53a) a substituted phenylsulfonyl grouphaving, on the ring, one or more, the same or different substituentsselected from a) a halogen atom, b) a cyano group, c) a nitro group, d)a C₁-C₆ alkyl group, e) a halo C₁-C₆ alkyl group, f) a C₁-C₆ alkoxygroup, g) a halo C₁-C₆ alkoxy group, h) a C₁-C₆ alkylthio group, i) ahalo C₁-C₆ alkylthio group, j) a C₁-C₆ alkylsulfinyl group, k) a haloC₁-C₆ alkylsulfinyl group, l) a C₁-C₆ alkylsulfonyl group, m) a haloC₁-C₆ alkylsulfonyl group, n) a mono C₁-C₆ alkylamino group, o) a diC₁-C₆ alkylamino group wherein the alkyl groups are the same ordifferent, and p) a C₁-C₆ alkoxycarbonyl group, 58a) a di C₁-C₆alkylaminothio group wherein the alkyl groups are the same or different,59a) a C₃-C₆ cycloalkylcarbonyl group, 61a) a C₁-C₆ alkyl C₃-C₆cycloalkylcarbonyl group, 63a) a phenyl C₁-C₆ alkylcarbonyl group, 64a)a substituted phenyl C₁-C₆ alkylcarbonyl group having, on the ring, oneor more, the same or different substituents selected from a) a halogenatom, b) a cyano group, c) a nitro group, d) a C₁-C₆ alkyl group, e) ahalo C₁-C₆ alkyl group, f) a C₁-C₆ alkoxy group, g) a halo C₁-C₆ alkoxygroup, h) a C₁-C₆ alkylthio group, i) a halo C₁-C₆ alkylthio group, j) aC₁-C₆ alkylsulfinyl group, k) a halo C₁-C₆ alkylsulfinyl group, l) aC₁-C₆ alkylsulfonyl group, m) a halo C₁-C₆ alkylsulfonyl group, n) amono C₁-C₆ alkylamino group, o) a di C₁-C₆ alkylamino group wherein thealkyl groups are the same or different, and p) a C₁-C₆ alkoxycarbonylgroup, 65a) a phenyl C₃-C₆ cycloalkylcarbonyl group, 66a) a substitutedphenyl C₃-C₆ cycloalkylcarbonyl group having, on the ring, one or more,the same or different substituents selected from a) a halogen atom, b) acyano group, c) a nitro group, d) a C₁-C₆ alkyl group, e) a halo C₁-C₆alkyl group, f) a C₁-C₆ alkoxy group, g) a halo C₁-C₆ alkoxy group, h) aC₁-C₆ alkylthio group, i) a halo C₁-C₆ alkylthio group, j) a C₁-C₆alkylsulfinyl group, k) a halo C₁-C₆ alkylsulfinyl group, l) a C₁-C₆alkylsulfonyl group, m) a halo C₁-C₆ alkylsulfonyl group, n) a monoC₁-C₆ alkylamino group, o) a di C₁-C₆ alkylamino group wherein the alkylgroups are the same or different, and p) a C₁-C₆ alkoxycarbonyl group,68a) a C₁-C₆ alkoxy C₁-C₆ alkylcarbonyl group, 73a) a C₁-C₆alkylcarbonyl C₁-C₆ alkylcarbonyl group, or 74a) a C₁-C₆ alkoxycarbonylC₁-C₆ alkylcarbonyl group, and more preferably 1a) a hydrogen atom, 4a)a C₁-C₆ alkylcarbonyl group, 5a) a halo C₁-C₆ alkylcarbonyl group, 17a)a C₁-C₁₀ alkoxy C₁-C₆ alkyl group, 18a) a halo C₁-C₆ alkoxy C₁-C₆ alkylgroup, 30a) a C₁-C₁₆ alkoxycarbonyl group, 32a) a halo C₁-C₆alkoxycarbonyl group or 64a) a C₁-C₆ alkoxy C₁-C₆ alkylcarbonyl group.

R² is preferably 1b) a hydrogen atom, 2b) a halogen atom, 6b) a hydroxygroup, 7b) a C₁-C₆ alkoxy group or 8b) a halo C₁-C₆ alkoxy group, andmore preferably 1b) a hydrogen atom or 7b) a C₁-C₆ alkoxy group.

G is preferably 1c) a C₂-C₁₀ alkyl group, 3c) a C₃-C₁₀ alkenyl group, or11c) a C₃-C₈ cycloalkyl C₁-C₆ alkyl group, and more preferably 1c) aC₂-C₁₀ alkyl group.

X is preferably 1d) a hydrogen atom, 2d) a halogen atom, or 5d) a C₁-C₆alkyl group, and more preferably 1d) a hydrogen atom.

Z is preferably an oxygen atom.

Y¹ is preferably 2e) a C₁-C₆ alkyl group, 3e) a halo C₁-C₆ alkyl group,or 4e) a C₂-C₆ alkenyl group, and more preferably 2e) a C₁-C₆ alkylgroup.

Y² is preferably 1f) a hydrogen atom, 2f) a halogen atom, 9f) a C₁-C₆alkyl group, 10f) a halo C₁-C₆ alkyl group, or 31f) a C₁-C₆ alkylthiogroup, and more preferably 1f) a hydrogen atom, 2f) a halogen atom, 9f)a C₁-C₆ alkyl group, or 10f) a halo C₁-C₆ alkyl group.

m is preferably 2.

In addition, a salt of a substituted aniline derivative represented bythe formula (II) is preferably an acid addition salt including, forexample, a carboxylate such as acetate, propionate, oxalate,trifluoroacetate, benzoate and the like; a sulfonate such asmethanesulfonate, trifluoromethanesulfonate, p-toluenesulfonate and thelike; an inorganic acid salt such as a hydrochloride, a sulfate, anitrate, a carbonate and the like.

A salt of 1,3-dimethyl-5-trifluoromethylpyrazole-4-carboxylic acid ofthe present invention includes a salt of an alkali metal (lithium,sodium, potassium, etc.); a salt of an alkaline earth metal (calcium,magnesium, etc.); an ammonium salt; and a salt of an organic amine(methylamine, triethylamine, diethanolamine, piperidine, pyridine,etc.).

A substituted pyrazolecarboxanilide derivative represented by theformula (I) or an intermediate thereof, i.e. a substituted anilinederivative represented by the formula (II), of the present invention maycontain one or plural numbers of asymmetric centers in the structuralformula, and further two or more optical isomers and diastereomers maybe present. Consequently, the present invention entirely encompasseseach optical isomer and the mixtures with any ratio thereof. Inaddition, a substituted pyrazolecarboxanilide derivative represented bythe formula (I) of the present invention may have two types of geometricisomers derived from a C—C double bond in the structural formula. Thepresent invention encompasses all of geometric isomers and the mixturescontaining them in any ratio. Moreover, the present inventionencompasses hydrates thereof.

Representative production methods for a substitutedpyrazolecarboxanilide derivative represented by the formula (I) and asubstituted aniline derivative represented by the formula (II), as anintermediate thereof are illustrated hereinbelow, but the presentinvention should not be construed as limiting thereto.

Production Method 1

(wherein G, R¹, X, n, Y¹, Y² and m are as defined above; and R³ is ahydrogen atom, a C₁-C₆ alkyl group, a halo C₁-C₆ alkyl group, a phenylgroup, a substituted phenyl group or a phenyl C₁-C₄ alkyl group; W is—O—, —S— or —N(R⁴)—, wherein R⁴ is a hydrogen atom, a C₁-C₆ alkyl group,a halo C₁-C₆ alkyl group, a phenyl group, a substituted phenyl group ora phenyl C₁-C₄ alkyl group; and Q is a halogen atom or a C₁-C₆ alkoxylgroup).

Among a substituted pyrazolecarboxanilide derivative represented by theformula (I), a substituted pyrazolecarboxanilide derivative (I-1)wherein Z is O, and R² is a hydrogen atom, a fluorine atom or WR³wherein W and R³ are as defined above can be produced by reacting ananiline derivative represented by the formulas (II-1) to (II-3) with apyrazolecarboxylic halide or a pyrazolecarboxylate ester represented bythe formula (III) in the presence or absence of a base in an inertsolvent, or by reacting an aniline derivative represented by theformulas (II-1) to (II-3) with a pyrazolecarboxylic acid represented bythe formula (IV) in the presence of a condensing agent, in the presenceor absence of a base, in an inert solvent, and any usual productionmethods for amides may be applicable.

An aniline derivative represented by the formula (II-2) can be producedby reducing an aniline derivative represented by the formula (II-1) inthe presence of a reducing agent, in an inert solvent.

An aniline derivative represented by the formula (II-3) can be producedby reacting an aniline derivative represented by the formula (II-1) withan alcohol derivative, a thiol derivative or an amine derivativerepresented by the formula (V), in the presence or absence of a base inan inert solvent.

The Formula (II-1)→the Formula (II-2)

An example of a reducing agent to be used in the present reactionincludes metal hydrides such as lithium aluminum hydride, lithiumborohydride, sodium borohydride, diisobutyl aluminum hydride, sodiumbis(2-methoxyethoxy)aluminum hydride and the like, metal such as lithiumand the like or metal salts, and the like. The amount of the reducingagent to be used may be selected, as appropriate, in the range fromequivalent to excess amount relative to an aniline derivativerepresented by the formula (II-1).

An example of an inert solvent to be used in the present reaction, whichmay be any one as long as it does not significantly inhibit progress ofthe present reaction, includes aromatic hydrocarbons such as benzene,toluene, xylene and the like; halogenated hydrocarbons such as methylenechloride, chloroform, carbon tetrachloride and the like; halogenatedaromatic hydrocarbons such as chlorobenzene, dichlorobenzene and thelike; straight chain or cyclic ethers such as diethyl ether, dioxane,tetrahydrofuran and the like, or dimethylsulfoxide and the like andthese inert solvents can be used alone or in combination of two or morekinds.

Reaction temperature may be in the range from room temperature toboiling temperature of an inert solvent to be used and reaction time maybe in the range from several minutes to 50 hours, while depending onreaction scale and reaction temperature.

After completion of the reaction, desired compound may be isolated fromthe reaction mixture by a conventional method and the desired compoundcan be produced by purification using recrystallization or columnchromatography, etc, if necessary. The desired compound may also besubjected to subsequent reaction step without isolation from thereaction mixture.

The formula (II-1)→the Formula (II-3)

An example of a base to be used in the present reaction includes metalhydrides such as lithium hydride, sodium hydride, potassium hydride andthe like; metal alcoholates such as sodium methoxide, sodium ethoxide,potassium tert-butoxide and the like; and alkyl metals such as n-butyllithium, sec-butyl lithium, tert-butyl lithium and the like. The amountof the base to be used may be selected, as appropriate, in the rangefrom equivalent to excess amount relative to an aniline derivativerepresented by the formula (II-1).

As an example of an inert solvent to be used in the present reaction,which may be any one as long as it does not significantly inhibitprogress of the present reaction, includes aromatic hydrocarbons such asbenzene, toluene, xylene and the like; alcohols such as methanol,ethanol and the like; straight chain or cyclic ethers such as diethylether, 1,2-dimethoxyethane, dioxane, tetrahydrofuran and the like, andthe like and these inert solvents can be used alone or in combination oftwo or more kinds.

Reaction temperature may be in the range from −70° C. to boilingtemperature of an inert solvent to be used and reaction time may be inthe range from several minutes to 50 hours, while depending on reactionscale and reaction temperature.

After completion of the reaction, desired compound may be isolated fromthe reaction mixture by a conventional method and the desired compoundcan be produced by purification using recrystallization or columnchromatography, etc, if necessary. The desired compound may also besubjected to subsequent reaction step without isolation from thereaction mixture.

The Formula (II-1), (II-2) or (II-3)→the Formula (I-1)

An example of a condensing agent to be used in the present reactionincludes diethyl cyanophosphate (DEPC), carbonyldiimidazole (CDI),1,3-dicyclohexylcarbodiimide (DCC), chloroformates,2-chloro-1-methylpyridinium iodide and the like.

As a base to be used in the present reaction, an inorganic base or anorganic base is included and an example of an inorganic base includesalkali metal hydroxides such as sodium hydroxide, potassium hydroxideand the like; alkali metal hydrides such as sodium hydride, potassiumhydride and the like; alkali metal salts of alcohol such as sodiumethoxide, potassium tert-butoxide and the like; carbonates such assodium carbonate, potassium carbonate, sodium hydrogen carbonate and thelike; and an example of organic bases includes triethylamine, pyridine,DBU and the like. The amount of the base to be used may be selected inthe range from equivalent to excess amount relative to apyrazolecarboxylic acid derivative represented by the formula (III) or(IV).

An example of an inert solvent to be used in the present reaction, whichmay be any one as long as it does not significantly inhibit progress ofthe present reaction, includes aromatic hydrocarbons such as benzene,toluene, xylene and the like; halogenated hydrocarbons such as methylenechloride, chloroform, carbon tetrachloride and the like; halogenatedaromatic hydrocarbons such as chlorobenzene, dichlorobenzene and thelike; straight chain or cyclic ethers such as diethyl ether, dioxane,tetrahydrofuran and the like; esters such as ethyl acetate and the like;amides such as dimethylformamide, dimethylacetamide and the like;dimethylsulfoxide; 1,3-dimethyl-2-imidazolidinone; acetone, methyl ethylketone and the like. These inert solvents can be used alone or incombination of two or more kinds.

As the present reaction is an equimolar reaction, each reactant may beused in equal mole, however, any of the reactants may also be used inexcess. Reaction temperature may be in the range from room temperatureto boiling temperature of an inert solvent to be used and reaction timemay be in the range from several minutes to 48 hours, while depending onreaction scale and reaction temperature.

After completion of the reaction, desired compound may be isolated fromthe reaction mixture by a conventional method and the desired compoundcan be produced by purification using recrystallization or columnchromatography, etc, if necessary.

An aniline derivative represented by the formula (II-1), as a rawmaterial of the present reaction, can be produced in accordance with aproduction method disclosed in JP-A-11-302233, JP-A-2001-122836 orJP-A-2006-8675.

A pyrazolecarboxylic acid derivative represented by the formulas (III)or (IV) can be produced in accordance with several methods described inknown literatures (for example, Aust. J. Chem., 1983, 36, 135-147,Synthesis, 1986, 753-755, JP-A-52-87168, JP-A-63-45264, JP-A-1-106866and the like).

Production Method 2

(wherein G, R¹, R², X, n, Y¹, Y² and m are as defined above).

Among substituted pyrazolecarboxanilide derivatives represented by theformula (I), a substituted pyrazolecarboxanilide derivative (I-2)wherein Z is S can be produced by reacting an anilide derivativerepresented by (I-1) with Lawesson's Reagent in accordance with a knownmethod (Tetrahedron Lett., 21 (42), 4061 (1980)).

Production Method 3

(wherein G, R², X, n, Y¹, Y², m and Q are as defined above and R^(1′) isas defined above except a hydrogen atom).

Among substituted pyrazolecarboxanilide derivatives represented by theformula (I), a substituted pyrazolecarboxanilide derivative (I-4)wherein R¹ is other than a hydrogen atom can be produced by reacting anamide derivative represented by the formula (I-3) with a halidederivative or an ester derivative represented by the formula (VI), inthe presence or absence of a base, in an inert solvent.

As an example of a base to be used in the present reaction includesmetal hydroxides such as sodium hydroxide, potassium hydroxide and thelike; carbonates such as sodium carbonate, potassium carbonate, sodiumhydrogen carbonate and the like; metal hydrides such as lithium hydride,sodium hydride, potassium hydride and the like; metal alcoholates suchas sodium methoxide, sodium ethoxide, potassium tert-butoxide and thelike; alkyl metals such as n-butyl lithium, sec-butyl lithium,tert-butyl lithium and the like. The amount of the base to be used maybe selected, as appropriate, in the range from equivalent to excessamount relative to an amide derivative represented by the formula (I-3).

An example of an inert solvent to be used in the present reaction, whichmay be any one as long as it does not significantly inhibit progress ofthe present reaction, includes aromatic hydrocarbons such as benzene,toluene, xylene and the like; alcohols such as methanol, ethanol and thelike; straight chain or cyclic ethers such as diethyl ether,1,2-dimethoxyethane, dioxane, tetrahydrofuran and the like; amides suchas dimethylformamide, dimethylacetamide and the like; dimethylsulfoxide;1,3-dimethyl-2-imidazolidinone and the like. These inert solvents can beused alone or in combination of two or more kinds.

Reaction temperature may be in the range from −70° C. to boilingtemperature of an inert solvent to be used and reaction time may be inthe range from several minutes to 50 hours, while depending on reactionscale and reaction temperature.

After completion of the reaction, desired compound may be isolated fromthe reaction mixture by a conventional method and the desired compoundcan be produced by purification using recrystallization or columnchromatography, etc, if necessary.

Production Method 4

(wherein G, R¹, R³, X, n, Y¹, Y² and m are as defined above, and q is 1or 2).

A substituted pyrazolecarboxanilide derivatives represented by theformula (I-6) can be produced by reacting a sulfide derivativerepresented by the formula (I-5) which can be produced in Productionmethod 1 with an oxidizing agent in the presence of an inert solvent

An example of an inert solvent to be used in the present reactionincludes halogenated hydrocarbons such as methylene chloride, chloroformand the like; aromatic hydrocarbons such as toluene, xylene and thelike; halogenated aromatic hydrocarbons such as fluorobenzene,chlorobenzene, dichlorobenzene and the like; acids such as acetic acidand the like; alcohols such as methanol, ethanol, propanol and the like.

An example of an oxidizing agent includes m-peroxychlorobenzoic acid,peracetic acid, potassium metaperiodate, potassium hydrogen persulphate(Oxone), hydrogen peroxide and the like. The amount of the oxidizingagent to be used may be selected, as appropriate, in the range of 0.5 to3 equivalents relative to a sulfide derivative represented by theformula (I-5).

Reaction temperature may be in the range from −50° C. to boilingtemperature of an inert solvent to be used and reaction time may be inthe range from several minutes to 24 hours, while depending on reactionscale and reaction temperature.

After completion of the reaction, desired compound may be isolated fromthe reaction mixture by a conventional method and the desired compoundcan be produced by purification using recrystallization or columnchromatography, etc, if necessary.

Typical compounds of substituted pyrazolecarboxanilide derivativesrepresented by the formula (I) are exemplified in Table 1 and Table 2,and typical compounds of substituted aniline derivatives represented bythe formula (II) are exemplified in Table 3, and an substitutedpyrazolecarboxylic acid derivative represented by the formula (IV) isexemplified in Table 4, however, the present invention should not beconstrued as limiting to these.

In “property” column of Table 1 and Table 2, melting point (° C.) orrefractive index (n_(D)(° C.)) is shown and for compounds described asamorphous or paste, ¹H-NMR data thereof were shown in Table 5. In theTables, “n-” is normal, and “i-” is iso, “t-” is tertiary, “c-” iscyclo, “Me” is a methyl group, “Et” is an ethyl group, “Pr” is a propylgroup, “Bu” is a butyl group, “Pen” is a pentyl group, “Hex” is a hexylgroup, “Ph” is a phenyl group, “Bn” is a benzyl group, “Ac” is an acetylgroup and “Pyr” is a pyrazinyl group.

TABLE 1 Formula (I-4)

No. G Y¹ Y² _(m) R¹ R² Property 1-1 Et Me 3,5-Me₂ H H 72-75 1-2 Et Me3,5-Me₂ Ac H 1-3 Et Me 3,5-Me₂ H OMe 129-131 1-4 Et Me 3,5-Me₂ Ac OMe1.5028(25.4) 1-5 Et Me 3,5-Me₂ COEt OMe 1-6 Et Me 3,5-Me₂ CO-c-Pr OMe118.8-121.6 1-7 Et Me 3,5-Me₂ CH₂OMe OMe 1-8 Et Me 3,5-Me₂ CH₂OEt OMe1.4889(24.2) 1-9 Et Me 3,5-Me₂ COOMe OMe 1-10 Et Me 3,5-Me₂ COOEt OMe77.2-79.2 1-11 Et Me 3,5-Me₂ COO-n-Pr OMe 1-12 Et Me 3,5-Me₂ COO-i-BuOMe 1.4895(25.4) 1-13 Et Me 3,5-Me₂ H OEt 110-113 1-14 Et Me 3,5-Me₂ AcOEt 1-15 Et Me 3,5-Me₂ COEt OEt 90-91 1-16 Et Me 3,5-Me₂ CO-c-Pr OEt119-120 1-17 Et Me 3,5-Me₂ CH₂OMe OEt 1-18 Et Me 3,5-Me₂ CH₂OEt OEt 1-19Et Me 3,5-Me₂ COOMe OEt 1-20 Et Me 3,5-Me₂ COOEt OEt 1-21 Et Me 3,5-Me₂COO-n-Pr OEt 1-22 Et Me 3,5-Me₂ COO-i-Bu OEt 1-23 Et Me 3-CF₃-5-Me H H1.4768(21.8) 1-24 Et Me 3-CF₃-5-Me Ac H 132-134 1-25 Et Me 3-CF₃-5-Me HOMe 57-60 1-26 Et Me 3-CF₃-5-Me Ac OMe 1.4736(24.6) 1-27 Et Me3-CF₃-5-Me COEt OMe 134-135 1-28 Et Me 3-CF₃-5-Me CO-c-Pr OMe1.4830(26.2) 1-29 Et Me 3-CF₃-5-Me CH₂OMe OMe 1-30 Et Me 3-CF₃-5-MeCH₂OEt OMe 1-31 Et Me 3-CF₃-5-Me COOMe OMe 128-130 1-32 Et Me 3-CF₃-5-MeCOOEt OMe 1.4697(25.9) 1-33 Et Me 3-CF₃-5-Me COO-n-Pr OMe 1-34 Et Me3-CF₃-5-Me COO-i-Bu OMe 1.4681(26.2) 1-35 Et Me 3-CF₃-5-Me H OEt 142-1451-36 Et Me 3-CF₃-5-Me Ac OEt 1.4720(24.5) 1-37 Et Me 3-CF₃-5-Me COEt OEt1.4710(26.9) 1-38 Et Me 3-CF₃-5-Me CO-c-Pr OEt 1-39 Et Me 3-CF₃-5-MeCH₂OMe OEt 1-40 Et Me 3-CF₃-5-Me CH₂OEt OEt 1-41 Et Me 3-CF₃-5-Me COOMeOEt 1-42 Et Me 3-CF₃-5-Me COOEt OEt 1-43 Et Me 3-CF₃-5-Me COO-n-Pr OEt1-44 Et Me 3-CF₃-5-Me COO-i-Bu OEt 1-45 n-Pr Me 3,5-Me₂ H H 167-168 1-46n-Pr Me 3,5-Me₂ Ac H 1-47 n-Pr Me 3,5-Me₂ H OMe 184-185 1-48 n-Pr Me3,5-Me₂ Ac OMe 1.4953(25.0) 1-49 n-Pr Me 3,5-Me₂ COEt OMe 1.4982(34.2)1-50 n-Pr Me 3,5-Me₂ CO-c-Pr OMe 1-51 n-Pr Me 3,5-Me₂ CH₂OMe OMe1.4979(22.1) 1-52 n-Pr Me 3,5-Me₂ CH₂OEt OMe 1.4942(22.7) 1-53 n-Pr Me3,5-Me₂ COOMe OMe 1.4980(22.7) 1-54 n-Pr Me 3,5-Me₂ COOEt OMe1.4952(23.0) 1-55 n-Pr Me 3,5-Me₂ COO-n-Pr OMe 1-56 n-Pr Me 3,5-Me₂COO-i-Bu OMe 1.4933(23.2) 1-57 n-Pr Me 3,5-Me₂ H QEt 178-179 1-58 n-PrMe 3,5-Me₂ Ac OEt 1-59 n-Pr Me 3,5-Me₂ COEt OEt 1.4980(22.7) 1-60 n-PrMe 3,5-Me₂ CO-c-Pr OEt 1-61 n-Pr Me 3,5-Me₂ CH₂OMe OEt 1-62 n-Pr Me3,5-Me₂ CH₂OEt OEt 1-63 n-Pr Me 3,5-Me₂ COOMe OEt 1-64 n-Pr Me 3,5-Me₂COOEt OE t 1-65 n-Pr Me 3,5-Me₂ COO-n-Pr OEt 1-66 n-Pr Me 3,5-Me₂COO-i-Bu OEt 1-67 n-Pr Me 3-CF₃-5-Me H H 131-133 1-68 n-Pr Me 3-CF₃-5-MeAc H 1-69 n-Pr Me 3-CF₃-5-Me H OMe 124 1-70 n-Pr Me 3-CF₃-5-Me Ac OMe1.4711(25.6) 1-71 n-Pr Me 3-CF₃-5-Me COEt OMe 1.4700(26.8) 1-72 n-Pr Me3-CF₃-5-Me CO-c-Pr OMe 1.4795(25.5) 1-73 n-Pr Me 3-CF₃-5-Me CH₂OMe OMe1-74 n-Pr Me 3-CF₃-5-Me CH₂OEt OMe 1.4658(26.9) 1-75 n-Pr Me 3-CF₃-5-MeCOOMe OMe 126-128 1-76 n-Pr Me 3-CF₃-5-Me COOEt OMe 1.4671(26.9) 1-77n-Pr Me 3-CF₃-5-Me COO-n-Pr OMe 1-78 n-Pr Me 3-CF₃-5-Me COO-i-Bu OMe1.4645(26.9) 1-79 n-Pr Me 3-CF₃-5-Me H OEt 1-80 n-Pr Me 3-CF₃-5-Me AcOEt 1-81 n-Pr Me 3-CF₃-5-Me COEt OEt 1-82 n-Pr Me 3-CF₃-5-Me CO-c-Pr OEt1-83 n-Pr Me 3-CF₃-5-Me CH₂OMe OEt 1-84 n-Pr Me 3-CF₃-5-Me CH₂OEt OEt1-85 n-Pr Me 3-CF₃-5-Me COOMe OEt 1-86 n-Pr Me 3-CF₃-5-Me COOEt OEt 1-87n-Pr Me 3-CF₃-5-Me COO-n-Pr OEt 1-88 n-Pr Me 3-CF₃-5-Me COO-i-Bu OEt1-89 n-Bu Me 3,5-Me₂ H H   150-151.5 1-90 n-Bu Me 3,5-Me₂ Ac H 1-91 n-BuMe 3,5-Me₂ H OMe 196-197 1-92 n-Bu Me 3,5-Me₂ Ac OMe 1-93 n-Bu Me3,5-Me₂ H OEt 1-94 n-Bu Me 3,5-Me₂ Ac OEt 1-95 n-Bu Me 3-CF₃-5-Me H H83-85 1-96 n-Bu Me 3-CF₃-5-Me Ac H 1-97 n-Bu Me 3-CF₃-5-Me H OMe 1-98n-Bu Me 3-CF₃-5-Me Ac OMe 1-99 n-Bu Me 3-CF₃-5-Me H OEt 1-100 n-Bu Me3-CF₃-5-Me Ac OEt 1-101 i-Bu Me 3-Me H H 141-144 1-102 i-Bu Me 3-Me EtOMe 1.4916(23.7) 1-103 i-Bu Me 3-Me Ac OMe 1.4961(26.4) 1-104 i-Bu Me3-Me COEt OMe 1.4973(26.2) 1-105 i-Bu Me 3-Me CO-c-Pr OMe 1.5014(25.5)1-106 i-Bu Me 3-Me CO(4-Me-Ph) OMe amorphous 1-107 i-Bu Me 3-MeCO(4-NO₂-Ph) OMe amorphous 1-108 i-Bu Me 3-Me COOMe OMe 95.5-97.8 1-109i-Bu Me 3-Me COOEt OMe 84.6-86.2 1-110 i-Bu Me 3-Me COO-n-Pr OMe86.7-88.4 1-111 i-Bu Me 3-Me COO-i-Bu OMe 91.8-94.0 1-112 i-Bu Me 3-MeCH₂OMe OMe 1.4919(24.0) 1-113 i-Bu Me 3-Me CH₂OEt OMe 1.4920(24.4) 1-114i-Bu Me 3-CF₃ H H 172-174 1-115 i-Bu Me 3-CF₃ Ac H 1-116 i-Bu Me 3-CF₃ HOMe amorphous 1-117 i-Bu Me 3-CF₃ Ac OMe 1-118 i-Bu Me 3-CF₃ H OEt 1-119i-Bu Me 3-CF₃ Ac OEt 1-120 i-Bu Et 3-CF₃ H H 175-176 1-121 i-Bu Me 5-CF₃H H 155-156 1-122 i-Bu Me 5-SMe H H 107-110 1-123 i-Bu Me 3,5-Me₂ H H148-151 1-124 i-Bu Me 3,5-Me₂ SO₂(4-F-Ph) H amorphous 1-125 i-Bu Me3,5-Me₂ Ac H 1.5021(22.5) 1-126 i-Bu Me 3,5-Me₂ COEt H 143.1-148.8 1-127i-Bu Me 3,5-Me₂ COPh H 51.3-65.3 1-128 i-Bu Me 3,5-Me₂ COCH₂CMe₃ H1.4859(22.0) 1-129 i-Bu Me 3,5-Me₂ CH₂OEt H 1.4882(23.8) 1-130 i-Bu Me3,5-Me₂ CH₂O(CH₂)₇Me H 1.4854(22.0) 1-131 i-Bu Me 3,5-Me₂ CH₂O(CH₂)₂OMeH 1.4889(21.9) 1-132 i-Bu Me 3,5-Me₂ CH₂OBn H 1.5212(21.9) 1-133 i-Bu Me3,5-Me₂ COOCH₂Cl H 121.1-124.8 1-134 i-Bu Me 3,5-Me₂ COOCH₂CCl₃ H143.1-145.6 1-135 i-Bu Me 3,5-Me₂ COO(CH₂)₂CH₂Cl H 117.1-121.4 1-136i-Bu Me 3,5-Me₂ COO-i-Bu H 122.2-138.0 1-137 i-Bu Me 3,5-Me₂ COO-t-Bu H 39.2 1-138 i-Bu Me 3,5-Me₂ COO(CH₂)₂OMe H 1.4750(23.5) 1-139 i-Bu Me3,5-Me₂ COO(CH₂)₁₅Me H 90.5-92.1 1-140 i-Bu Me 3,5-Me₂ Ac OMe1.5016(23.3) 1-141 i-Bu Me 3,5-Me₂ COEt OMe 1.4981(23.5) 1-142 i-Bu Me3,5-Me₂ CO-i-Pr OMe 82.5-83   1-143 i-Bu Me 3,5-Me₂ COPh OMe1.5219(23.7) 1-144 i-Bu Me 3,5-Me₂ CH₂OMe OMe 1.4944(23.1) 1-145 i-Bu Me3,5-Me₂ CH₂OEt OMe 1.4892(22.2) 1-146 i-Bu Me 3,5-Me₂ CH₂O(CH₂)₂OMe OMe1.4885(25.1) 1-147 i-Bu Me 3,5-Me₂ COOMe OMe 1.4926(23.2) 1-148 i-Bu Me3,5-Me₂ COOEt OMe 1.4894(23.2) 1-149 i-Bu Me 3,5-Me₂ COOCH₂Cl OMe1.4941(21.5) 1-150 i-Bu Me 3,5-Me₂ COO-n-Pr OMe 1.4928(22.2) 1-151 i-BuMe 3,5-Me₂ COO-i-Pr OMe 1.4884(23.0) 1-152 i-Bu Me 3,5-Me₂ COO-i-Bu OMe1.4829(22.3) 1-153 i-Bu Me 3,5-Me₂ COOCH₂CMe₃ OMe 1.4864(23.0) 1-154i-Bu Me 3,5-Me₂ COO(CH₂)₂OMe OMe 1.4959(23.0) 1-155 i-Bu Me 3,5-Me₂ HOMe 189-190 1-156 i-Bu Me 3,5-Me₂ Et OMe amorphous 1-157 i-Bu Me 3,5-Me₂CH₂CCl₃ OMe 1.4939(22.2) 1-158 i-Bu Me 3,5-Me₂ Ac OEt 1.4940(26.4) 1-159i-Bu Me 3,5-Me₂ COEt OEt 1.4921(26.5) 1-160 i-Bu Me 3,5-Me₂ CO-i-Pr OEtpaste 1-161 i-Bu Me 3,5-Me₂ COPh OEt 1-162 i-Bu Me 3,5-Me₂ CH₂OMe OEt1-163 i-Bu Me 3,5-Me₂ CH₂OEt OEt 1-164 i-Bu Me 3,5-Me₂ CH₂O(CH₂)₂OMe OEt1-165 i-Bu Me 3,5-Me₂ COOMe OEt 1-166 i-Bu Me 3,5-Me₂ COOEt OEt 1-167i-Bu Me 3,5-Me₂ COOCH₂Cl OEt 1-168 i-Bu Me 3,5-Me₂ COO-n-Pr OEt 1-169i-Bu Me 3,5-Me₂ COO-i-Pr OEt 1-170 i-Bu Me 3,5-Me₂ COO-i-Bu OEt 1-171i-Bu Me 3,5-Me₂ COOCH₂CMe₃ OEt 1-172 i-Bu Me 3,5-Me₂ COO(CH₂)₂OMe OEt1-173 i-Bu Me 3,5-Me₂ H OEt 165-166 1-174 i-Bu Me 3,5-Me₂ Et OEt 1-175i-Bu Me 3,5-Me₂ CH₂CCl₃ OEt 1-176 i-Bu Et 3,5-Me₂ H H 127-128 1-177 i-BuMe 3,5-Me₂ H F 136.5-137.5 1-178 i-Bu Me 3,5-Me₂ Et H 1.4904(25.7) 1-179i-Bu Me 3-Me-5-F H H 169.5-171   1-180 i-Bu Me 3-Me-5-F H OMe 135-1371-181 i-Bu Me 3-Me-5-F Et OMe 1.4825(26.0) 1-182 i-Bu Me 3-Me-S-F Ac OMe 86.4 1-183 i-Bu Me 3-Me-5-F COPh OMe 124.1-130.8 1-184 i-Bu Me 3-Me-5-FCOOMe OMe 64.5-80.5 1-185 i-Bu Me 3-Me-5-F COO-i-Bu OMe 1.4789(23.7)1-186 i-Bu Me 3-Me-5-F COO(CH₂)₂OMe OMe 1.4857(22.3) 1-187 i-Bu Me3-Me-5-F CH₂OEt OMe 1.4804(23.8) 1-188 i-Bu Me 3-Me-5-Cl H H 160-1611-189 i-Bu Me 3-Me-5-Cl H OMe 144-146 1-190 i-Bu Me 3-Me-5-Cl Me OMe1.4919(25.6) 1-191 i-Bu Me 3-Me-5-Cl Et OMe 1.4938(26.0) 1-192 i-Bu Me3-Me-5-Cl CH₂OMe OMe 1.4961(26.0) 1-193 i-Bu Me 3-Me-5-Cl CH₂OEt OMe1.4932(25.6) 1-194 i-Bu Me 3-Me-5-Cl COOMe OMe 1.4883(25.6) 1-195 i-BuMe 3-Me-5-Cl COOEt OMe 1.4915(26.0) 1-196 i-Bu Me 3-Me-5-Cl COO-i-Bu OMe1.4850(25.6) 1-197 i-Bu Me 3-Me-5-Cl COO(CH₂)₂OMe OMe 1.4946(26.0) 1-198i-Bu Me 3-Me-5-Cl Ac OMe 102.6-102.8 1-199 i-Bu Me 3-Me-5-Cl COEt OMe101.8-104.2 1-200 i-Bu Me 3-Me-5-Cl COPh OMe 1.5210(26.0) 1-201 i-Bu Et3-Me-5-Cl H H 104.5-106   1-202 i-Bu Me 3-Me-5-I H H 152-153 1-203 i-BuMe 3-Me-5-CF₃ H OMe 88-89 1-204 i-Bu Me 3-Me-5-CF₃ Ac OMe 1.4710(25.7)1-205 i-Bu Me 3-Me-5-CF₃ COOMe OMe 1.4672(25.7) 1-206 i-Bu Me 3-Me-5-CF₃CH₂OEt OMe 1.4652(25.7) 1-207 i-Bu Me 3-CF₃-5-Me H H 1.4869(23.4) 1-208i-Bu Me 3-CF₃-5-Me Ac H   152-152.5 1-209 i-Bu Me 3-CF₃-5-Me COOMe H148.5-150   1-210 i-Bu Me 3-CF₃-5-Me CH₂OEt H 1.4623(22.8) 1-211 i-Bu Me3-CF₃-5-Me H OMe 138-139 1-212 i-Bu Me 3-CF₃-5-Me COOMe OMe 1.4729(20.7)1-213 i-Bu Me 3-CF₃-5-Me COOEt OMe 1.4695(20.7) 1-214 i-Bu Me 3-CF₃-5-MeCOOCH₂CH═CH₂ OMe 1.4742(24.5) 1-215 i-Bu Me 3-CF₃-5-Me COO(CH₂)₂Me OMe1.4685(20.7) 1-216 i-Bu Me 3-CF₃-5-Me COO(CH₂)₃Me OMe 1.4689(24.5) 1-217i-Bu Me 3-CF₃-5-Me COO-i-Bu OMe 1.4669(22.6) 1-218 i-Bu Me 3-CF₃-5-MeCOOPh OMe 50-55 1-219 i-Bu Me 3-CF₃-5-Me COO(CH₂)₂OMe OMe 1.4691(22.3)1-220 i-Bu Me 3-CF₃-5-Me COSMe OMe 1.4870(24.9) 1-221 i-Bu Me 3-CF₃-5-MeCOSEt OMe 1.4862(24.9) 1-222 i-Bu Me 3-CF₃-5-Me CH₂OMe OMe 1.4669(22.4)1-223 i-Bu Me 3-CF₃-5-Me CH₂OEt OMe 108-110 1-224 i-Bu Me 3-CF₃-5-Me AcOMe 1.4720(20.6) 1-225 i-Bu Me 3-CF₃-5-Me CO-c-Pr OMe 1.4735(24.8) 1-226i-Bu Me 3-CF₃-5-Me H OEt 1-227 i-Bu Me 3-CF₃-5-Me Ac OEt 1-228 i-Bu Me3-CF₃-5-Cl H H 136-137 1-229 i-Bu Me 3-CF₃-5-Cl Ac H 1-230 i-Bu Me3-CF₃-5-Cl H OMe 130-132 1-231 i-Bu Me 3-CF₃-5-Cl Ac OMe 1-232 i-Bu Me3-CF₃-5-Cl H OEt 1-233 i-Bu Me 3-CF₃-5-Cl Ac OEt 1-234 (CH₂)₄Me Me3,5-Me₂ H H 128-130 1-235 (CH₂)₄Me Me 3,5-Me₂ Ac H 1-236 (CH₂)₄Me Me3,5-Me₂ H OMe 1-237 (CH₂)₄Me Me 3,5-Me₂ Ac OMe 1-238 (CH₂)₄Me Me 3,5-Me₂H OEt 1-239 (CH₂)₄Me Me 3,5-Me₂ Ac OEt 1-240 (CH₂)₄Me Me 3-CF₃-5-Me H H1-241 (CH₂)₄Me Me 3-CF₃-5-Me Ac H 1-242 (CH₂)₄Me Me 3-CF₃-5-Me H OMe1-243 (CH₂)₄Me Me 3-CF₃-5-Me Ac OMe 1-244 (CH₂)₄Me Me 3-CF₃-5-Me H OEt1-245 (CH₂)₄Me Me 3-CF₃-5-Me Ac OEt 1-246 CH₂CMe₃ Me 3,5-Me₂ H H 174-1761-247 CH₂CMe₃ Me 3,5-Me₂ Ac H 1-248 CH₂CMe₃ Me 3,5-Me₂ H OMe 1-249CH₂CMe₃ Me 3,5-Me₂ Ac OMe 1-250 CH₂CMe₃ Me 3,5-Me₂ H OEt 1-251 CH₂CMe₃Me 3,5-Me₂ Ac OEt 1-252 CH₂CMe₃ Me 3-CF₃-5-Me H H 1-253 CH₂CMe₃ Me3-CF₃-5-Me Ac H 1-254 CH₂CMe₃ Me 3-CF₃-5-Me H OMe 1-255 CH₂CMe₃ Me3-CF₃-5-Me Ac OMe 1-256 CH₂CMe₃ Me 3-CF₃-5-Me H OEt 1-257 CH₂CMe₃ Me3-CF₃-5-Me Ac OEt 1-258 CH₂CH(Me)Et Me 3,5-Me₂ H H 67-70 1-259CH₂CH(Me)Et Me 3,5-Me₂ Ac H 1-260 CH₂CH(Me)Et Me 3,5-Me₂ H OMe 158-1601-261 CH₂CH(Me)Et Me 3,5-Me₂ Ac OMe 1-262 CH₂CH(Me)Et Me 3,5-Me₂ H OEt1-263 CH₂CH(Me)Et Me 3,5-Me₂ Ac OEt 1-264 CH₂CH(Me)Et Me 3-CF₃-5-Me H H1-265 CH₂CH(Me)Et Me 3-CF₃-5-Me Ac H 1-266 CH₂CH(Me)Et Me 3-CF₃-5-Me HOMe 143-144 1-267 CH₂CH(Me)Et Me 3-CF₃-5-Me Ac OMe 1-268 CH₂CH(Me)Et Me3-CF₃-5-Me H OEt 1-269 CH₂CH(Me)Et Me 3-CF₃-5-Me Ac OEt 1-270 CH₂CHEt₂Me 3,5-Me₂ H H 67-70 1-271 CH₂CHEt₂ Me 3,5-Me₂ Ac H 1-272 CH₂CHEt₂ Me3,5-Me₂ H OMe 1-273 CH₂CHEt₂ Me 3,5-Me₂ Ac OMe 1-274 CH₂CHEt₂ Me 3,5-Me₂H OEt 1-275 CH₂CHEt₂ Me 3,5-Me₂ Ac OEt 1-276 CH₂CHEt₂ Me 3-CF₃-5-Me H H1-277 CH₂CHEt₂ Me 3-CF₃-5-Me Ac H 1-278 CH₂CHEt₂ Me 3-CF₃-5-Me H OMe1-279 CH₂CHEt₂ Me 3-CF₃-5-Me Ac OMe 1-280 CH₂CHEt₂ Me 3-CF₃-5-Me H OEt1-281 CH₂CHEt₂ Me 3-CF₃-5-Me Ac OEt 1-282 (CH₂)₂CHMe₂ Me 3,5-Me₂ H H152-153 1-283 (CH₂)₂CHMe₂ Me 3,5-Me₂ Ac H 1-284 (CH₂)₂CHMe₂ Me 3,5-Me₂ HOMe 166-167 1-285 (CH₂)₂CHMe₂ Me 3,5-Me₂ Ac OMe 1.4925(21.8) 1-286(CH₂)₂CHMe₂ Me 3,5-Me₂ H OEt 1-287 (CH₂)₂CHMe₂ Me 3,5-Me₂ Ac OEt 1-288(CH₂)₂CHMe₂ Me 3-CF₃-5-Me H H 1-289 (CH₂)₂CHMe₂ Me 3-CF₃-5-Me Ac H 1-290(CH₂)₂CHMe₂ Me 3-CF₃-5-Me H OMe 138-140 1-291 (CH₂)₂CHrMe₂ Me 3-CF₃-5-MeAc OMe 1-292 (CH₂)₂CHMe₂ Me 3-CF₃-5-Me H OEt 1-293 (CH₂)₂CHMe₂ Me3-CF₃-5-Me Ac OEt 1-294 (CH₂)₇Me Me 3,5-Me₂ H H 1.5052(23.3) 1-295(CH₂)₇Me Me 3,5-Me₂ Ac H 1-296 (CH₂)₇Me Me 3,5-Me₂ H OMe 1-297 (CH₂)₇MeMe 3,5-Me₂ Ac OMe 1-298 (CH₂)₇Me Me 3,5-Me₂ H OEt 1-299 (CH₂)₇Me Me3,5-Me₂ Ac OEt 1-300 (CH₂)₇Me Me 3-CF₃-5-Me H H 1-301 (CH₂)₇Me Me3-CF₃-5-Me Ac H 1-302 (CH₂)₇Me Me 3-CF₃-5-Me H OMe 1-303 (CH₂)₇Me Me3-CF₃-5-Me Ac OMe 1-304 (CH₂)₇Me Me 3-CF₃-5-Me H OEt 1-305 (CH₂)₇Me Me3-CF₃-5-Me Ac OEt 1-306 n-Pr Me 3-Me-5-CF₃ H H 141-143 1-307 n-Pr Me3-Me-5-CF₃ H OMe 152-153 1-308 n-Pr Me 3-Me-5-CF₃ Ac OMe 1.4688(25.6)1-309 n-Pr Me 3-Me-5-CF₃ Ac H 112-113 1-310 i-Bu Me 3-CF₃-5-Me CH₂OMe H1.4690(25.9) 1-311 i-Bu Me 3-Me-5-F COOCH₂CH₂Cl OMe 1.4966(24.7) 1-312i-Bu Me 3,5-Me₂ COOCH₂CH₂Cl OMe 1.5039(24.8) 1-313 i-Bu Me 3,5-Me₂COCH₂CMe₃ OMe 1.4914(24.8) 1-314 i-Bu Me 3,5-Me₂ CO-c-Pr OMe1.5061(24.9) 1-315 i-Bu Me 3-CF₃-5-Me COEt H 171-173 1-316 i-Bu ClCH₂CH₂3,5-Me₂ H OMe 170-171 1-317 i-Bu ClCH₂CH₂ 3,5-Me₂ Ac OMe 1.4955(24.8)1-318 i-Bu Me 3,5-Me₂ CO-n-Pr OMe 1.4943(24.8) 1-319 i-Bu Me 3,5-Me₂CO-t-Bu OMe 113-115 1-320 i-Bu Me 3,5-Me₂ CO(4-MeO-Ph) OMe 1.5198(25.3)1-321 i-Bu Me 3,5-Me₂ CO(4-Me-Ph) OMe 1.5139(25.0) 1-322 i-Bu Me 3,5-Me₂CO(4-Cl-Ph) OMe 51-64 1-323 n-Pr Me 3-Me-5-CF₃ COEt OMe 1.4705(26.8)1-324 i-Bu Me 3,5-Me₂ CO(3-Cl-Ph) OMe 1.5266(25.4) 1-325 i-Bu Me 3,5-Me₂CO(3-Me-Ph) OMe 1.5182(25.5) 1-326 i-Bu Me 3,5-Me₂ CO(3-Me-OPh) OMe1.5165(26.5) 1-327 i-Bu Me 3,5-Me₂ CO(2-Me-Ph) OMe  88-128 1-328 i-Bu Me3,5-Me₂ CO(2-Cl-Ph) OMe 121-122 1-329 i-Bu Me 3,5-Me₂ CO(2-MeO-Ph) OMe57-83 1-330 i-Bu Me 3,5-Me₂ COCH═CH₂ OMe 1.5088(24.5) 1-331 i-Bu Me3,5-Me₂ COCHClMe OMe amorphous 1-332 i-Bu Me 3,5-Me₂ CO(3-Me-2-Pyr) OMe52-64 1-333 i-Bu Me 3,5-Me₂ SNEt₂ OMe 1-334 i-Bu Me 3-CF₃-5-Me CO-i-Pr H161-163 1-335 Et Me 3-CF₃-5-Me CO-i-Pr OMe 1.4680(26.4) 1-336 i-Bu Me3,5-Me₂ CO-t-Pen OMe 95-96 1-337 i-Bu Me 3,5-Me₂ COCH₂OMe OMe1.4939(26.5) 1-338 i-Bu Me 3,5-Me₂ CO(4-CF₃-Ph) OMe  54 1-339 i-Bu Me3,5-Me₂ COCH₂Ph OMe 1-340 i-Bu Me 3,5-Me₂ COCH═CMe₂ OMe 1.5091(26.5)1-341 i-Bu Me 3,5-Me₂ COCH═CHMe OMe 1.5082(26.5) 1-342 i-Bu Me 3,5-Me₂COCH₂CH₂COOEt OMe 100-101 1-343 n-Pr Me 3-CF₃-5-Me COOCH₂CH═CH₂ OMe1.4728(27.0) 1-344 n-Pr Me 3-CF₃-5-Me CO-t-Bu OMe 1.4715(26.9) 1-345n-Pr Me 3-CF₃-5-Me CO-n-Pr OMe 1.4660(26.8) 1-346 Et Me 3-CF₃-5-MeCOOCH₂CH₂OMe OMe 1.4695(26.2) 1-347 Et Me 3-CF₃-5-Me CO-t-Bu OMe1.4730(26.2) 1-348 i-Bu Me 3,5-Me₂ COCMe₂CH₂Cl OMe 1.5062(26.7) 1-349i-Bu Me 3,5-Me₂ CO-c-Pen OMe 1.5019(26.8) 1-350 i-Bu CH═CH₂ 3,5-Me₂ HOMe 124-130 1-351 i-Bu CH═CH₂ 3,5-Me₂ CO-i-Pr OMe 1.5044(25.8) 1-352i-Bu Me 3,5-Me₂ CO(2,4-Cl₂-Ph) OMe 1.5220(26.1) 1-353 i-Bu Me 3,5-Me₂CO(3,4-Cl₂-Ph) OMe  53 1-354 n-Pr Me 3,5-Me₂ CO-i-Pr OMe 1.5075(25.1)1-355 n-Pr Me 3-CF₃-5-Me CO-i-Pr OMe 1.4741(25.8) 1-356 Et Me 3-CF₃-5-MeCOOCH₂CH═CH₂ OMe 1.4781(25.9) 1-357 n-Pr Me 3,5-Me₂ CO-t-Bu OMe1.4888(26.0) 1-358 n-Pr Me 3,5-Me₂ CO(4-Cl-Ph) OMe  41 1-359 Et Me3,5-Me₂ n-Pen OMe 1.4897(25.0) 1-360 Et Me 3,5-Me₂ CH₂(4-F-Ph) OMe  107.9 1-361 Et Me 3,5-Me₂ CO-c-Bu OMe 1.4939(32.1) 1-362 Et Me 3,5-Me₂CO-i-Pr OMe 100.3-103.4 1-363 Et Me 3,5-Me₂ CO-s-Bu OMe 1.5031(22.9)1-364 Et Me 3,5-Me₂ CO-t-Bu OMe 108 1-365 Et Me 3,5-Me₂ COCMe₂Et OMe1.4983(20.5) 1-366 Et Me 3,5-Me₂ COCH₂OMe OMe 1.4958(21.6) 1-367 Et Me3,5-Me₂ COCHEt₂ OMe 1.4991(21.8) 1-368 Et Me 3,5-Me₂ CO-c-Pen OMe1.4977(30.5) 1-369 Et Me 3,5-Me₂ CO-c-Hex OMe 1.4934(25.2) 1-370 Et Me3,5-Me₂ COCH₂OPh OMe amorphous 1-371 Et Me 3,5-Me₂ COCH₂-t-Bu OMe1.4962(32.1) 1-372 Et Me 3,5-Me₂ CO(4-CF₃-Ph) OMe 1.5023(32.2) 1-373 EtMe 3,5-Me₂

OMe 1.4211(32.0) 1-374 Et Me 3,5-Me₂ CH₂OCH₂CH₂OMe OMe 1.4892(31.0)1-375 Et Me 3,5-Me₂ CH₂O-i-Pr OMe 1.4855(30.2) 1-376 Et Me 3,5-Me₂CH₂O-i-Bu OMe 1.4849(33.2) 1-377 Et Me 3,5-Me₂ CH₂O-n-Pr OMe1.4982(23.1) 1-378 Et Me 3,5-Me₂ CH₂O-n-Bu OMe 1.4940(23.2) 1-379 Et Me3,5-Me₂ COOCH₂CCl₃ OMe 145.2-145.8 1-380 Et Me 3,5-Me₂ COO-n-Pen OMe1.4960(20.2) 1-381 Et Me 3-CF₃-5-Me COEt H 127-128 1-382 Et Me3-CF₃-5-Me CO-c-Bu OMe 1.4818(19.1) 1-383 Et Me 3-CF₃-5-Me CO-s-Bu OMe1.4701(24.4) 1-384 Et Me 3-CF₃-5-Me COCHEt₂ OMe 1.4724(24.3) 1-385 Et Me3-CF₃-5-Me CH₂O-n-Bu OMe 1.4670(23.7) 1-386 Et Me 3-CF₃-5-Me CH₂O-i-BuOMe 1.4659(21.8) 1-387 Et Me 3-CF₃-5-Me CH₂O-n-Pr OMe 1.4672(21.8) 1-388Et Me 3-Me-5-Cl H OMe 127.3-128.5 1-389 Et Me 3-Me-5-Cl CO-i-Pr OMe134.1-135.4 1-390 Et Me 3-Me-5-Cl CO-c-Bu OMe 136.1-137.2 1-391 Et Me3-Me-5-Cl CO-t-Bu OMe 108.6-110.4 1-392 Et Me 3-Me-5-Cl COO-i-Bu OMe1.4931(32.1) 1-393 Et Me 3-Me-5-Cl CH₂O-i-Pr OMe 1.4884(30.5) 1-394 EtMe 3-Me-5-Cl CH₂O-n-Bu OMe 1.4875(29.1) 1-395 Et Me 3-Me H OMe183.8-185.4 1-396 Et Me 3-Me CO-i-Pr OMe 114.4-114.9 1-397 Et Me 3-MeCO-c-Pen OMe 1.4975(31.0) 1-398 Et Me 3-Me CH₂O-i-Pr OMe 1.4902(23.4)1-399 Et Me 3,5-Me₂ CO-n-Pr OEt 1.4932(23.0) 1-400 Et Me 3,5-Me₂ CO-i-PrOEt 80-81 1-401 n-Pr Me 3,5-Me₂ COOCH₂CH═CH₂ OMe 1.4841(23.7) 1-402 n-PrMe 3,5-Me₂ COOCH₂CHEt-n-Bu OMe 1.4894(23.8) 1-403 n-Pr Me 3,5-Me₂COCH₂OMe OMe paste 1-404 n-Pr Me 3,5-Me₂ Me OMe 1.4983(22.0) 1-405 n-PrMe 3,5-Me₂ Et OMe 1.4970(20.0) 1-406 n-Pr Me 3,5-Me₂ CH₂CH═CH₂ OMe1.5019(23.2) 1-407 n-Pr Me 3,5-Me₂ (CH₂)₇Me OMe 1.4880(23.5) 1-408 n-PrMe 3-CF₃-5-Me COOMe H 140-145 1-409 n-Pr Me 3-CF₃-5-Me COOEt H 129-1301-410 n-Pr Me 3-CF₃-5-Me COEt H 140-145 1-411 n-Pr Me 3-CF₃-5-Me CO-i-PrH 135-137 1-412 n-Pr Me 3-CF₃-5-Me CH₂O-n-Pr OMe 1.4673(21.8) 1-413 n-PrMe 3-CF₃-5-Me CH₂O-t-Bu OMe 1.4669(21.7) 1-414 i-Bu Me 3,5-Me₂ Me OMepaste 1-415 i-Bu Me 3,5-Me₂ n-Pr OMe paste 1-416 i-Bu Me 3,5-Me₂CH₂CH═CH₂ OMe 70-71 1-417 i-Bu Me 3,5-Me₂ CH₂(4-NO₂-Ph) OMe paste 1-418i-Bu Me 3,5-Me₂ CH₂Ph OMe 90-97 1-419 i-Bu Me 3,5-Me₂ CH₂(4-Me-Ph) OMepaste 1-420 i-Bu Me 3,5-Me₂ CH₂O-n-Pr OMe 59-65 1-421 i-Bu Me 3,5-Me₂CH₂O-n-Bu OMe paste 1-422 i-Bu Me 3,5-Me₂ CH₂O-i-Pr OMe paste 1-423 i-BuMe 3,5-Me₂ CH₂O-i-Bu OMe 80-82 1-424 i-Bu Me 3,5-Me₂ CH₂O-t-Bu OMe paste1-425 i-Bu Me 3,5-Me₂ CH₂O-s-Bu OMe paste 1-426 i-Bu Me 3,5-Me₂CH₂OCH₂CF₃ OMe paste 1-427 i-Bu Me 3,5-Me₂ CH₂OCH₂CH═CH₂ OMe paste 1-428i-Bu Me 3,5-Me₂ CH₂O(CH₂)₇Me OMe paste 1-429 i-Bu Me 3,5-Me₂ CO-c-Bu OMepaste 1-430 i-Bu Me 3,5-Me₂ CO-s-Bu OMe 106.1-107.8 1-431 i-Bu Me3,5-Me₂ COCHEt₂ OMe  97.2-101.8 1-432 i-Bu Me 3,5-Me₂ COCMe₂Br OMe 93-106 1-433 i-Bu Me 3,5-Me₂ CO-c-Hex OMe 1.5035(24.7) 1-434 i-Bu Me3,5-Me₂ CH₂(2,4,6- OMe 64.2-66.7 Cl₃-Ph) 1-435 i-Bu Me 3,5-Me₂

OMe 1.4991(20.5) 1-436 i-Bu Me 3,5-Me₂ COCHMeOMe OMe 1.4977(20.6) 1-437i-Bu Me 3,5-Me₂ COCMe₂OMe OMe 1.4906(23.6) 1-438 i-Bu Me 3,5-Me₂ COOPhOMe 135.3-136.1 1-439 i-Bu Me 3-Me-5-CF₃ COO-i-Bu OMe 1.4733(21.2) 1-440i-Bu Me 3-Me-5-CF₃ CO-t-Bu OMe 1.4745(21.2) 1-441 i-Bu Me 3-Me-5-CF₃CO-i-Pr OMe 1.4722(32.1) 1-442 i-Bu Me 3-Me-5-CF₃ CO-c-Pr OMe1.4780(32.0) 1-443 i-Bu Me 3-CF₃-5-Me COEt OMe 1.4727(24.1) 1-444 i-BuMe 3-CF₃-5-Me CO-i-Pr OMe 1.4720(24.2) 1-445 i-Bu Me 3-CF₃-5-MeCH₂O-n-Pr OMe 1.4658(22.7) 1-446 i-Bu Me 3-CF₃-5-Me CH₂O-n-Bu OMe1.4670(22.5) 1-447 i-Bu Me 3-CF₃-5-Me CH₂O-i-Bu OMe 1.4625(21.9) 1-448i-Bu Me 3-Me-5-F CO-t-Bu OMe amorphous 1-449 i-Bu Me 3-Me-5-Cl CO-i-PrOMe   124-124.4 1-450 i-Bu Me 3-Me-5-Cl CO-t-Bu OMe 1.4860(31.4) 1-451i-Bu Me 3-Me-5-Cl CO-c-Bu OMe   114-115.3 1-452 i-Bu Me 3-Me-5-ClCOCH₂OMe OMe amorphous 1-453 i-Bu Me 3-Me-5-Cl CO-c-Pen OMe 136.2-137  1-454 i-Bu Me 3-Me-5-Cl CH₂O-n-Pr OMe 1.4887(31.6) 1-455 i-Bu Me3-Me-5-Cl CH₂O-i-Bu OMe 60.7-64.7 1-456 i-Bu Me 3-Me CO-i-Pr OMe67.3-68.2 1-457 i-Bu Me 3-Me CO-t-Bu OMe 124.1-125.5 1-458 i-Bu Me 3-MeCO-s-Bu OMe 1.4914(32.0) 1-459 i-Bu Me 3-Me CO-c-Bu OMe   83-88.6 1-460i-Bu Me 3-Me CO-c-Pen OMe 1.4990(31.7) 1-461 i-Bu Me 3-Me COCHEt₂ OMe1.4905(28.5) 1-462 i-Bu Me 3-Me CH₂O-i-Pr OMe 1.4817(31.7) 1-463 i-Bu H3,5-Me₂ H OMe 82.8-90.5 1-464 i-Bu Et 3,5-Me₂ H OMe 162-163 1-465 i-BuCH₂CF₃ 3,5-Me₂ H OMe 176-177 1-466 i-Bu Me 3,5-Me₂ CO-i-Pr F1.4860(22.7) 1-467 CH₂CHMeEt Me 3,5-Me₂ COEt OMe 1.4929(20.1) 1-468CH₂CHMeEt Me 3,5-Me₂ CO-i-Pr OMe 1.4910(20.0) 1-469 n-Bu Me 3,5-Me₂ COEtOMe 1.4895(20.6) 1-470 n-Bu Me 3,5-Me₂ CO-i-Pr OMe 1.4835(18.9) 1-471CH₂CH-c-Pen Me 3-CF₃5-Me H H 200201 1-472 CH₂CH₂CHMe₂ Me 3,5-Me₂ COEtOMe 1.4960(20.5) 1-473 CH₂CH₂CHMe₂ Me 3,5-Me₂ CO-i-Pr OMe 1.4950(21.6)1-474 Et i-Pr 3,5-Me₂ H OEt 173-174 1-475 Et i-Pr 3,5-Me₂ Ac OEt 88-891-476 Et Me 3,5-Me₂ H O-n-Pr 104-105 1-477 Et Me 3,5-Me₂ CO-n-Pr O-n-Pr1.4833(33.0) 1-478 Et Me 3,5-Me₂ CO-i-Pr O-n-Pr 1.4919(33.0) 1-479 Et Me3,5-Me₂ CO-t-Bu O-n-Pr 1.4848(32.0) 1-480 Et Me 3,5-Me₂ CH₂OEt O-n-Pr1.4729(23.5) 1-481 Et Me 3-I-5-Me H H 134-135 1-482 Et Me 3,5-Me₂COCHMeCOEt OEt 1-483 n-Pr Me 3,5-Me₂ CO-n-Pr OMe 1.4959(31.2) 1-484 n-PrMe 3,5-Me₂ CO-s-Bu OMe 1.4960(32.3) 1-485 n-Pr Me 3,5-Me₂ CO-c-Pen OMe1.4880(29.0) 1-486 n-Pr Me 3,5-Me₂ CH₂O-n-Pr OMe 1.4869(28.0) 1-487 n-PrMe 3,5-Me₂ CH₂O-i-Pr OMe 1.4819(29.3) 1-488 n-Pr Me 3-Me-5-Cl H OMe135.4-139.0 1-489 n-Pr Me 3-Me-5-Cl CO-i-Pr OMe 128.1-128.2 1-490 n-PrMe 3-Me-5-Cl CO-s-Bu OMe 99.2-99.7 1-491 n-Pr Me 3-Me-5-Cl CO-c-Pr OMe123.0-123.9 1-492 n-Pr Me 3-Me 5-Cl CO-c-Pen OMe 141.7-142.1 1-493 n-PrMe 3-Me-5-Cl CH₂OEt OMe 1.4954(20.7) 1-494 n-Pr Me 3-I-5-Me H H 183-1851-495 n-Pr Me 3-Me H OMe 146.8-147.0 1-496 n-Pr Me 3-Me CO-i-Pr OMe61.6-62.9 1-497 n-Pr Me 3-Me CO-s-Bu OMe 1.4960(22.2) 1-498 n-Pr Me 3-MeCO-c-Pen OMe 1.4991(22.1) 1-499 n-Pr Me 3-Me CH₂O-n-Pr OMe 1.4864(22.8)1-500 n-Pr Me 3-Me CH₂O-i-Pr OMe 1.4863(22.4) 1-501 n-Pr Me 3,5-Me₂CO-n-Pr OEt 1.4892(22.7) 1-502 n-Pr Me 3,5-Me₂ CO-i-Pr OEt 1.4910(22.8)1-503 n-Pr Me 3,5-Me₂ H O-n-Pr   158-159.5 1-504 n-Pr Me 3,5-Me₂ COEtO-n-Pr 1.4975(20.5) 1-505 n-Pr Me 3,5-Me₂ CO-n-Pr O-n-Pr 1.4940(20.5)1-506 n-Pr Me 3,5-Me₂ CO-i-Pr O-n-Pr 1.4960(20.6) 1-507 i-Bu CH₂CF₃3,5-Me₂ COEt OMe 137-138 1-508 i-Bu CH₂CF₃ 3,5-Me₂ CO-i-Pr OMe 1-509i-Bu i-Pr 3,5-Me₂ H OMe 166-167 1-510 i-Bu i-Pr 3,5-Me₂ CO-i-Pr OMe107-108 1-511 i-Bu Me 3-Me-5-Cl H F 143.2-144.7 1-512 i-Bu Me 3-Me-5-ClCO-i-Pr F 1.4888(23.0) 1-513 i-Bu Me 3-Cl-5-Me H OMe 153-161 1-514 i-BuMe 3-Cl-5-Me CO-i-Pr OMe paste 1-515 i-Bu Me 3-Cl-5-Me CH₂O-i-Pr OMepaste 1-516 i-Bu Me 3-Cl-5-Me COOMe OMe amorphous 1-517 i-Bu Me3-Br-5-Me H OMe 172-174 1-518 i-Bu Me 3-Br-5-Me CO-i-Pr OMe paste 1-519i-Bu Me 3-Br-5-Me CH₂O-i-Pr OMe paste 1-520 i-Bu Me 3-I-5-Me H H 178-1831-521 i-Bu Me 3-Br-5-Me COOMe OMe paste 1-522 i-Bu Me 3-I-5-Me H OMeamorphous 1-523 i-Bu Me 3-I-5-Me COOMe OMe paste 1-524 i-Bu Me 3-I-5-MeCO-i-Pr OMe paste 1-525 i-Bu Me 3-I-5-Me CH₂OEt OMe 100-103 1-526 i-BuMe 3-I-5-Me CH₂O-i-Pr OMe 100-102 1-527 i-Bu Me 3,5-Me₂ CH₂CH═CMe₂ OMe81-83 1-528 CH═CMe₂ Me 3,5-Me₂ H OMe 1-529 i-Bu Me 5-CF₃ H OMe 170 1-530i-Bu Me 5-CF₃ CO-i-Pr OMe 1.4680(22.8) 1-531 i-Bu Et 3,5-Me₂ CO-i-Pr OMe1.4913(23.0) 1-532 CH═CMe₂ Me 3,5-Me₂ CO-i-Pr OMe 1-533 i-Bu Me 3,5-Me₂CO-n-Pr OEt 1.4870(22.5) 1-534 i-Bu Me 3,5-Me₂ H O-n-Pr 138-139 1-535i-Bu Me 3-I H OMe 210-218 1-536 i-Bu Me 3-Br H OMe 203 1-537 i-Bu Me3-Cl H OMe 174-182 1-538 i-Bu Me 3,5-Cl₂ H OMe 132 1-539 i-Bu Me 3-ICO-i-Pr OMe paste 1-540 i-Bu Me 3-Br CO-i-Pr OMe paste 1-541 i-Bu Me3-Cl CO-i-Pr OMe paste 1-542 i-Bu Me 3-CF₃ CO-i-Pr OMe paste 1-543 i-BuMe 3,5-Cl₂ CO-i-Pr OMe 113-114 1-544 i-Bu Me 3,5-Me₂

F amorphous 1-545 i-Bu Me 3,5-Me₂

F amorphous 1-546 i-Bu Me 3,5-Me₂

OMe 150.4-151.2 1-547 i-Bu Me 3,5-Me₂ CH₂OAc OMe 94-95 1-548 i-Bu Me3,5-Me₂ CH₂OC(═O)Et OMe  99 1-549 i-Bu Me 3,5-Me₂ CH₂OC(═O)-i-Pr OMe 1121-550 i-Bu Me 3,5-Me₂ COSMe OMe 1-551 i-Bu Me 3,5-Me₂ COSEt OMe

TABLE 2 Formula (I-4)

No. G Xn Y² _(m) R¹ R² Property 2-1 Et 6-Me 3,5-Me₂ H H 2-2 Et 6-Me3,5-Me₂ Ac H 2-3 Et 6-Me 3,5-Me₂ H OMe 2-4 Et 6-Me 3,5-Me₂ Ac OMe 2-5 Et6-Me 3,5-Me₂ H OEt 2-6 Et 6-Me 3,5-Me₂ Ac OEt 2-7 Et 6-Me 3-CF₃-5-Me H H2-8 Et 6-Me 3-CF₃-5-Me Ac H 2-9 Et 6-Me 3-CF₃-5-Me H OMe 2-10 Et 6-Me3-CF₃-5-Me Ac OMe 2-11 Et 6-Me 3-CF₃-5-Me H OEt 2-12 Et 6-Me 3-CF₃-5-MeAc OEt 2-13 n-Pr 6-Me 3,5-Me₂ H H 128-131 2-14 n-Pr 6-Me 3,5-Me₂ Ac H2-15 n-Pr 6-Me 3,5-Me₂ H OMe 132-134 2-16 n-Pr 6-Me 3,5-Me₂ Ac OMe1.4905(25.9) 2-17 n-Pr 6-Me 3,5-Me₂ H OEt 154-155 2-18 n-Pr 6-Me 3,5-Me₂Ac OEt 2-19 n-Pr 6-Me 3-CF₃-5-Me H H 2-20 n-Pr 6-Me 3-CF₃-5-Me Ac H 2-21n-Pr 6-Me 3-CF₃-5-Me H OMe 104-106 2-22 n-Pr 6-Me 3-CF₃-5-Me Ac OMe1.4751(26.7) 2-23 n-Pr 6-Me 3-CF₃-5-Me H OEt 152-153 2-24 n-Pr 6-Me3-CF₃-5-Me Ac OEt 2-25 n-Pr 6-Me 3-Me-5-Cl H OMe   127-128.5 2-26 n-Pr6-Me 3-CF₃-5-Me COEt OMe 151-152 2-27 i-Bu 6-Cl 3,5-Me₂ H OMe 106-1092-28 i-Bu 6-Cl 3,5-Me₂ Ac OMe amorphous 2-29 Et 6-Me 3,5-Me₂ CO-c-Pr OMe138-140 2-30 Et 6-Me 3,5-Me₂ COEt OMe 132-134 2-31 Et 6-Me 3-CF₃-5-MeCO-n-Pr OMe 1.4960(26.6) 2-32 n-Pr 6-Me 3-CF₃-5-Me COOMe OMe 165-1662-33 i-Bu 6-Me 3,5-Me₂ H OMe 126-127 2-34 n-Pr 6-Me 3,5-Me₂ CO-i-Pr OMe1.4955(33.5) 2-35 n-Pr 6-Me 3,5-Me₂ CO-t-Bu OMe 128.5-130.2 2-36 n-Pr6-Me 3,5-Me₂ COCHEt₂ OMe 1.4918(32.6) 2-37 n-Pr 6-Me 3,5-Me₂ COO-i-BuOMe 1.4870(30.1) 2-38 i-Bu 6-Me 3,5-Me₂ COEt OMe amorphous 2-39 Et 6-Me3,5-Me₂ CO-i-Pr OMe 1.4952 (32.0) 2-40 n-Pr 6-Me 3-Me H OMe amorphous2-41 n-Pr 6-Me 3-Me CO-i-Pr OMe paste 2-42 n-Pr 6-Me 3,5-Me₂ CO-i-Pr OEt111-112 2-43 i-Bu 6-Me 3,5-Me₂ CO-i-Pr OMe 38-42 2-44 n-Pr 6-Me3-CF₃-5-Me CO-i-Pr OMe 155 2-45 i-Bu 6-Me 3-CF₃-5-Me H OMe 68-70 2-46n-Pr 6-Me 3,5-Me₂ H OH 192-195

TABLE 3 Formula (II)

No G Xn R² ¹H-NMR [CDCl₃/TMS, δ value (ppm)] 3-1 n-Pr 6-Me F 7.09 (s, 1H), 6.54 (s, 1 H), 3.76 (bs, 2 H), 2.63 (m, 2 H), 2.13 (s, 3 H), 1.58(m, 2 H), 0.96 (t, 3 H) 3-2 n-Pr 6-Me H 7.18 (s, 1 H), 6.54 (s, 1 H),4.45-4.20 (br, 2 H), 4.27 (m, 1 H), 2.50 (dd, 2 H), 2.14 (s, 3 H), 1.57(m, 2 H), 0.98 (t, 3 H) 3-3 n-Pr 6-Me OMe 7.10 (s, 1 H), 6.66 (s, 1 H),3.72 (bs, 2 H), 3.42 (s, 3 H), 2.84 (m, 2 H), 2.14 (s, 3 H), 1.61 (m, 2H), 1.00 (t, 3 H) 3-4 Et 6-Me F 7.09 (s, 1 H), 6.56 (s, 1 H), 3.78 (bs,2 H), 2.71 (m, 2 H), 2.14 (s, 3 H), 1.19 (td, 3 H) 3-5 Et 6-Me OMe 7.10(s, 1 H), 6.68 (s, 1 H), 3.75 (bs, 2 H), 3.41 (s, 3 H), 2.91 (dd, 2 H),2.15 (s, 3 H), 1.22 (t, 3 H) 3-6 Et H O-n-Pr 7.22 (d, 1 H), 6.67 (d, 1H), 6.52 (dd, 1 H), 3.80 (br, 2 H), 3.46 (t, 2 H), 2.92 (dd, 2 H), 1.69(dd, 2 H), 1.21 (t, 3 H), 0.94 (t, 3 H) 3-7 n-Pr H O-n-Pr 7.22 (d, 1 H),6.66 (d, 1 H), 6.51 (dd, 1 H), 3.78 (br, 2 H), 3.47 (t, 2 H), 2.85 (m, 2H), 1.70 (dd, 2 H), 1.60 (m, 2 H), 1.00 (t, 3 H), 0.94 (t, 3 H) 3-8 i-BuH O-n-Pr 7.24 (d, 1 H), 6.70 (d, 1 H), 6.53 (dd, 1 H), 3.79 (bs, 2 H),3.47 (t, 2 H), 2.81 (d, 2 H), 2.10 (m, 1 H), 1.70 (m, 2 H), 0.95 (t, 3H), 0.91 (d, 6 H)

TABLE 4 Formula (IV)

No Y¹ Y²m melting point (° C.) 4-1 Me 3-Me-5-CF₃ 124-125.5

TABLE 5 No. ¹H-NMR[CDCl₃/TMS, δ value (ppm)] 1-106 7.61(d, 2H), 7.52(d,1H), 7.17(m, 4H), 7.11(m, 1H), 3.69(s, 3H), 3.47(s, 3H), 2.86(d, 2H),2.39(s, 3H), 2.37(s, 3H), 1.96(m, 1H), 0.73(d, 6H) 1-107 8.27(d, 2H),7.83(d, 2H), 7.59(d, 1H), 7.22(d, 1H), 7.17(m, 1H), 6.97(s, 1H), 3.66(s,3H), 3.51(s, 3H), 2.91(d, 2H), 2.36(s, 3H), 1.97(m, 1H), 0.77(d, 6H)1-116 8.04(s, 1H), 7.73(br, 1H), 7.72(d, 1H), 7.50(d, 1H), 7.43(dd, 1H),4.01(s, 3H), 3.47(s, 3H), 2.93(d, 2H), 2.21(m, 1H), 0.94(d, 6H) 1-1247.80(dd, 2H), 7.49(d, 1H), 7.13(dd, 2H), 7.02(dd, 1H), 6.89(d, 1H),4.40-4.31(m, 1H), 3.57(s, 3H), 2.42(d, 2H), 2.28(s, 3H), 2.22(s, 3H),1.70-1.59(m, 1H), 0.78(d, 6H) 1-156 7.41(d, 1H), 7.01(dd, 1H), 6.96(d,1H), 3.98(dd, 2H), 3.56(s, 3H), 3.44(s, 3H), 2.79(d, 2H), 2.06(s, 3H),2.00(s, 3H), 1.86(m, 1H), 1.25(dd, 3H), 0.74(d, 6H) 1-160 7.47(d, 1H),7.16-7.05(m, 2H), 3.67(3, 3H), 3.60(dd, 2H), 3.04(m, 1H), 2.88(d, 2H),2.37(s, 3H), 2.25(s, 3H), 1.97(m, 1H), 1.31(t, 3H), 1.26(d, 6H), 0.77(d,6H) 1-331 7.48(d, 1H), 7.10(d, 1H), 7.08(s, 1H), 5.11(q, 1H), 3.64(s,3H), 3.45(s, 3H), 2.96(dd, 1H), 2.74(dd, 1H), 2.31(s, 3H), 2.24(s, 3H),1.92(m, 1H), 1.77(d, 3H), 0.84(d, 3H), 0.65(d, 3H) 1-370 7.41(d, 1H),7.28(m, 2H), 7.08(d, 1H), 6.98(m, 2H), 6.84(m, 2H), 4.98(s, 2H), 3.63(s,3H), 3.40(s, 3H), 2.96(q, 2H), 2.18(s, 3H), 2.14(s, 3H), 1.26(t, 3H)1-403 7.43(d, 1H), 7.14(d, 1H), 7.18(m, 1H), 4.32(s, 2H), 3.66(s, 3H),3.43(s, 3H), 3.39(s, 3H), 2.92(m, 2H), 2.31(s, 3H), 2.23(s, 3H), 1.51(m,2H), 0.94(t, 3H) 1-414 7.41(d, 1H), 7.01(m, 2H), 3.58(s, 3H), 3.48(s,3H), 3.44(s, 3H), 2.79(d, 2H), 2.06(s, 3H), 2.00(s, 3H), 1.85(m, 1H),0.76(d, 6H) 1-415 7.39(d, 1H), 7.00(dd, 1H), 6.97(d, 1H), 3.88(m, 2H),3.56(s, 3H), 3.44(s, 3H), 2.78(d, 2H), 2.05(s, 3H), 2.00(s, 3H), 1.84(m,1H), 1.66(m, 2H), 0.95(t, 3H), 0.75(d, 6H) 1-417 8.18(d, 2H), 7.50(d,2H), 7.38(d, 1H), 6.95(dd, 1H), 6.88(d, 1H), 5.22(s, 2H), 3.58(s, 3H),3.41(s, 3H), 2.73(d, 2H), 2.08(s, 3H), 1.99(s, 3H), 1.73(m, 1H), 0.70(d,6H) 1-419 7.33(d, 1H), 7.23(d, 2H), 6.93(dd, 1H), 6.89(d, 1H), 6.83(d,2H), 5.06(s, 2H), 3.79(s, 3H), 3.56(s, 3H), 3.40(s, 3H), 2.73(d, 2H),2.05(s, 3H), 2.01(s, 3H), 1.74(m, 1H), 0.70(d, 6H) 1-421 7.40(d, 1H),7.16(m, 2H), 5.30(s, 2H), 3.61(t, 2H), 3.59(s, 3H), 3.43(s, 3H), 2.80(d,2H), 2.09(s, 3H), 2.04(s, 3H), 1.87(m, 1H), 1.59(m, 2H), 1.37(m, 2H),0.91(t, 3H), 0.76(d, 6H) 1-422 7.39(d, 1H), 7.18(m, 2H), 5.31(s, 2H),3.91(m, 1H), 3.59(s, 3H), 3.43(s, 3H), 2.80(d, 2H), 2.08(s, 3H), 2.04(s,3H), 1.87(m, 1H), 1.22(d, 6H), 0.77(d, 6H) 1-424 7.39(d, 1H), 7.23(m,2H), 5.23(s, 2H), 3.58(s, 3H), 3.43(s, 3H), 2.80(d, 2H), 2.07(s, 6H),1.89(m, 1H), 1.26(s, 9H), 0.78(d, 6H) 1-425 7.39(d, 1H), 7.17(m, 2H),5.43(d, 1H), 5.22(d, 1H), 3.68(m, 1H), 3.59(s, 3H), 3.43(s, 3H), 2.80(d,2H), 2.08(s, 3H), 2.04(s, 3H), 1.87(m, 1H), 1.46-1.63(m, 2H), 1.20(d,3H), 0.89(t, 3H), 0.77(dd, 6H) 1-426 7.42(d, 1H), 7.10(m, 2H), 5.43(s,H), 4.14(q, 2H), 3.58(s, 3H), 3.44(s, 3H), 2.80(d, 2H), 2.05(s, 3H),2.01(s, 3H), 1.85(m, 1H), 0.76(d, 6H) 1-427 7.40(d, 1H), 7.17(dd, 1H),7.13(d, 1H), 5.87-5.98(m, 1H), 5.32(s, 2H), 5.29(dd, 1H), 5.20(dd, 1H),4.16(d, 2H), 3.59(s, 3H), 3.44(s, 3H), 2.80(d, 2H), 2.09(s, 3H), 2.04(s,3H), 1.87(m, 1H), 0.76(d, 6H) 1-428 7.39(d, 1H), 7.15(m, 2H), 5.30(s,2H), 3.60(t, 2H), 3.59(s, 3H), 3.43(s, 3H), 2.80(d, 2H), 2.09(s, 3H),2.04(s, 3H), 1.88(m, 1H), 1.60(m, 2H), 1.27(m, 10H), 0.88(t, 3H),0.77(d, 6H) 1-429 7.49(d, 1H), 7.12(d, 1H), 7.08(dd, 1H), 3.68(s, 3H),3.46(m, 1H), 3.46(s, 3H), 2.88(d, 2H), 2.40(m, 2H), 2.35(s, 3H), 2.25(s,3H), 1.84-2.11(m, 5H), 0.80(d, 6H) 1-448 7.49(d, 1H), 7.06(d, 1H),6.98(m, 1H), 3.64(s, 3H), 3.47(s, 3H), 2.86(d, 2H), 2.39(s, 3H), 1.95(m,1H), 1.38(s, 9H), 0.76(d, 6H) 1-452 7.49(d, 1H), 7.18(d, 1H), 7.13(m,1H), 4.31(s, 2H), 3.71(s, 3H), 3.46(s, 3H), 3.42(s, 3H), 2.88(d, 2H),2.32(s, 3H), 2.03(m, 1H), 0.79(d, 6H) 1-514 7.53(d, 1H), 7.27(d, 1H),7.16(dd, 1H), 3.72(s, 3H), 3.48(s, 3H), 2.92(d, 2H), 2.88(m, 1H),2.43(s, 3H), 2.07(m, 1H), 1.21(d, 6H), 0.84(d, 6H) 1-515 7.41(d, 1H),7.21(s, 1H), 7.19(d, 1H), 5.28(s, 2H), 3.92(m, 1H), 3.63(s, 3H), 3.44(s,3H), 2.82(d, 2H), 2.19(s, 3H), 1.94(m, 1H), 1.21(d, 6H), 0.79(d, 6H)1-516 7.55(d, 1H), 7.32(d, 1H), 7.16(dd, 1H), 3.79(s, 3H), 3.76(s, 3H),3.49(s, 3H), 2.94(d, 2H), 2.47(s, 3H), 2.14(m, 1H), 0.92(d, 6H) 1-5187.53(d, 1H), 7.28(d, 1H), 7.18(dd, 1H), 3.74(s, 3H), 3.47(s, 3H),2.92(m, 1H), 2.91(d, 2H), 2.42(s, 3H), 2.07(m, 1H), 1.23(d, 6H), 0.84(d,6H) 1-519 7.42(d, 1H), 7.22(d, 1H), 7.21(s, 1H), 5.28(s, 2H), 3.94(m,1H), 3.63(s, 3H), 3.44(s, 3H), 2.82(d, 2H), 2.14(s, 3H), 1.95(m, 1H),1.21(d, 6H), 0.79(d, 6H) 1-521 7.56(d, 1H), 7.35(d, 1H), 7.19(dd, 1H),3.81(s, 3H), 3.76(s, 3H), 3.50(s, 3H), 2.94(d, 2H), 2.47(s, 3H), 2.14(m,1H), 0.92(d, 6H) 1-522 8.17(br, 1H), 7.78(d, 1H), 7.47-7.53(m, 2H),3.84(s, 3H), 3.47(s, 3H), 2.93(d, 2H), 2.62(s, 3H), 2.24(m, 1H), 0.95(d,6H) 1-523 7.57(d, 1H), 7.39(d, 1H), 7.22(dd, 1H), 3.84(s, 3H), 3.76(s,3H), 3.50(s, 3H), 2.95(d, 2H), 2.46(s, 3H), 2.15(m, 1H), 0.92(d, 6H)1-524 7.51(d, 1H), 7.27(d, 1H), 7.20(dd, 1H), 3.74(s, 3H), 3.46(s, 3H),2.99(m, 1H), 2.90(d, 2H), 2.37(s, 3H), 2.07(m, 1H), 1.26(d, 6H), 0.82(d,6H) 1-539 7.55(d, 1H), 7.16(d, 1H), 7.11(dd, 1H), 6.87(s, 1H), 3.73(s,3H), 3.48(s, 3H), 3.31(m, 1H), 2.89(d, 2H), 2.04(m, 1H), 1.27(d, 6H),0.79(d, 6H) 1-540 7.55(d, 1H), 7.20(d, 1H), 7.12(dd, 1H), 7.05(s, 1H),3.72(s, 3H), 3.49(s, 3H), 3.22(m, 1H), 2.90(d, 2H), 2.05(m, 1H), 1.26(d,6H), 0.81(d, 6H) 1-541 7.56(d, 1H), 7.21(d, 1H), 7.15(s, 1H), 7.12(dd,1H), 3.72(s, 3H), 3.49(s, 3H), 3.17(m, 1H), 2.91(d, 2H), 2.05(m, 1H),1.25(d, 6H), 0.82(d, 6H) 1-542 7.57(d, 1H), 7.17(d, 1H), 7.09(dd, 1H),7.06(s, 1H), 3.78(s, 3H), 3.49(s, 3H), 3.26(m, 1H), 2.90(d, 2H), 2.03(m,1H), 1.24(d, 6H), 0.78(d, 6H) 1-544 7.51(d, 1H), 7.16(m, 1H), 6.97(d,1H), 3.82(s, 3H), 3.65(s, 3H), 2.63(t, 2H), 2.27(s, 3H), 2.24(s, 3H),2.10(s, 3H), 2.00(s, 3H), 1.67(m, 1H), 0.81(d, 6H) 1-545 7.47(d, 1H),7.34(d, 1H), 7.11(m, 1H), 6.94(d, 1H), 6.86(d, 1H), 3.67(s, 3H), 2.60(t,2H), 2.51(s, 3H), 2.38(s, 3H), 2.28(s, 3H), 1.73(m, 1H), 0.75(d, 6H)2-28 7.62(s, 1H), 7.25(s, 1H), 3.71(s, 3H), 3.50(s, 3H), 2.88(d, 2H),2.38(s, 3H), 2.32(s, 3H), 2.24(s, 3H), 2.02(m, 1H), 0.85(d, 6H) 2-387.41(s, 1H), 7.12(s, 1H), 3.72(s, 3H), 3.48(s, 3H), 2.88(d, 2H), 2.38(s,3H), 2.30(s, 3H), 2.24(s, 3H), 2.40-2.30(m, 2H), 2.04(m, 1H), 1.14(t,3H), 0.85(d, 6H) 2-40 8.26(s, 1H), 7.82(s, 1H), 7.27(br, 2H), 3.90(s,3H), 3.45(s, 3H), 2.95(m, 2H), 2.57(s, 3H), 2.32(s, 3H), 1.71(m, 2H),1.02(t, 3H) 2-41 7.37(s, 1H), 7.10(s, 1H), 6.30(s, 1H), 3.59(s, 3H),3.47(s, 3H), 3.43(m, 1H), 2.92(br, 2H), 2.48(s, 3H), 2.17(s, 3H),1.55(br, 2H), 1.28(d, 6H), 0.94(t, 3H)

The agrohorticultural agent, in particular, agrohorticulturalinsecticides or acaricides, containing a substitutedpyrazolecarboxanilide derivative represented by the formula (I) or saltof the present invention as an active ingredient, are suitable forcontrolling various insect pests such as agrohorticultural insect pests,stored grain insect pests, sanitary insect pests, nematodes, etc., whichare injurious to paddy rice, fruit trees, vegetables, other crops,flowers and ornamental plants, etc. They have a marked insecticidaleffect, for example, on LEPIDOPTERA including summer fruit tortrix(Adoxophes orana fasciata), smaller tea tortrix (Adoxophyes sp.),Manchurian fruit moth (Grapholita inopinata), oriental fruit moth(Grapholita molesta), soybean pod borer (Leguminivora glycinivorella),mulberry leafroller (Olethreutes mori), tea leafroller (Caloptiliathevivora), Caloptilia sp. (Caloptilia zachrysa), apple leafminer(Phyllonorycter ringoniella), pear barkminer (Spulerrina astaurota),common white (Piers rapae crucivora), tobacco budworm (Heliothis sp.),codling moth (Laspey resia pomonella), diamondback moth (Plutellaxylostella), apple fruit moth (Argyresthia conjugella), peach fruit moth(Carposina niponensis), rice stem borer (Chilo suppressalis), riceleafroller (Cnaphalocrocis medinalis), tobacco moth (Ephestia elutella),mulberry pyralid (Glyphodes pyloalis), yellow rice borer (Scirpophagaincertulas), rice skipper (Parnara guttata), rice armyworm (Pseudaletiaseparata), pink borer (Sesamia inferens), common cutworm (Spodopteralitura), beet armyworm (Spodoptera exigua), etc.;

HEMIPTERA including aster leafhopper (Macrosteles fascifrons), greenrice leafhopper (Nephotettix cincticepts), brown rice planthopper(Nilaparvata lugens), whitebacked rice planthopper (Sogatellafurcifera), citrus psylla (Diaphorina citri), grape whitefly(Aleurolibus taonabae), sweetpotato whitefly (Bemisia tabaci),greenhouse whitefly (Trialeurodes vaporariorum), turnup aphid (Lipaphiserysimi), green peach aphid (Myzus persicae), Indian wax scale(Ceroplastes ceriferus), cottony citrus scale (Pulvinaria aurantii),camphor scale (Pseudaonidia duplex), san Jose scale (Comstockaspisperniciosa), arrowhead scale (Unaspis yanonensis), etc.;TYLENCHIDA including soybean beetle (Anomala rufocuprea), Japanesebeetle (Popillia japonica), tobacco beetle (Lasioderma serricorne),powderpost beetle (Lyctus brunneus), twenty-eight-spotted ladybird(Epilachna vigintiotopunctata), azuki bean weevil (Callosobruchuschinensis), vegetable weevil (Listroderes costirostris), maize weevil(Sitophilus zeamais), boll weevil (Anthonomus grandis grandis), ricewater weevil (Lissorhoptrus oryzophilus), cucurbit leaf beetle(Aulacophora femoralis), rice leaf beetle (Oulema oryzae), striped fleabeetle (Phyllotreta striolata), pine shoot beetle (Tomicus piniperda),Colorado potato beetle (Leptinotarsa decemlineata), Mexican bean beetle(Epilachna varivestis), corn rootworm (Diabrotica sp.), etc.;DIPTERA including melon fly (Dacus (Zeugodacus) cucurbitae), orientalfruit fly (Dacus (Bactrocera) dorsalis), rice leafminer (Agnomyzaoryzae), onion maggot (Delia antiqua), seedcorn maggot (Delia platura),soybean pod gall midge (Asphondylia sp.), etc.; TYLENCHIDA includingroot-lesion nematode (Pratylenchus sp.), potato cyst nematode (Globoderarostochiensis), root-knot nematode (Meloidogyne sp.), citrus nematode(Tylenchulus semipenetrans), Aphelenchus sp. (Aphelenchus avenae),chrysanthemum foliar (Aphelenchoides ritzemabosi), etc.; and ACARINAincluding citrus red mite (Panonychus citri), fruit tree red spider mite(Panonychus ulmi), carmine spider mite (Tetranychus cinnabarinus),Kanzawa spider mite (Tetranychus Kanzawai Kishida), two-spotted spidermite (Tetranychus urticae Koch), pink tea rust mite (Acaphylla theae),pink citrus rust mite (Aculops pelekassi), purple tea mice (Calacaruscarinatus), pear rust mite (Epitrimerus pyri), etc.

A substituted pyrazolecarboxanilide derivative represented by theformula (I) or salts thereof of the present invention is used preferablyas agrohorticultural insecticides or acaricides. However, the compoundexhibits excellent control effect against various insect pests such asinsect pests for forest and wood, insect pests for livestock farming,sanitary insect pests, etc. and can be used as pest control agents invarious wide fields. Examples of insect pests include: Tabanidae such asTabanus rufidens Bigot; Muscidae such as housefly (Musca domesticauicina MACQUART); Gasterophilidae such as horse bot fly (Gasterophilusintestinalis); Hypodermatidae such as cattle grub (Hypoderma bouis L.);Phoridae such as Megaselia spiracularis; Culicidae such as pale housemosquito (Culex pipiens pallens), Anopheles sinensis, one-stripedmosquito (Aedes albopictus), and Aedes japonicus; Pulicidae such as catflea (Ctenocephalides felis), dog flea (Ctenocephalides canis), humanflea (Pulex irritans); Ixodidae such as Ixodes ovatus Neumann;Lymantriidae such as Euproctis similes; Rhynchophoridae such as riceweevil (Sitophilus zeamais); Vespidae such as Vespa simillimaxanthoptera Cameron; Blattellidae such as German cockroach (Blattelagermanica); Blattidae such as American cockroach (Periplaneta americana)and Periplaneta japonica; Pthiridae such as public-louse (Phthiruspubis); Termitidae such as Japanese termite (Reticulitermes speratus)and house termite (Coptotermes formosanus); and Ixodidae such as Ixodespersulcatus; and Macronyssidae such as tropical rat mite (Ornithonyssusbacoti).

The agrohorticultural agent, in particular, agrohorticulturalinsecticides or acaricides, containing a substitutedpyrazolecarboxanilide derivative represented by the formula (I) or saltthereof of the present invention as an active ingredient has a markedcontrolling effect on the above-exemplified insect pests, which areinjurious to paddy field crops, upland crops, fruit trees, vegetablesand other crops, flowers and ornament plants, and the like. Therefore,the desired effect of the agrohorticultural insecticides of the presentinvention can be exhibited by applying the agents to paddy field, field,fruit trees, vegetables, other crops, seeds of flowers and ornamentplants, paddy field water, stalks and leaves, or soil at a season atwhich the insect pests are expected to appear, before their appearanceor at the time when their appearance is confirmed.

Plants, for which an agrohorticultural agent of the present inventioncan be used, are not specifically limited and include, for example,plants shown hereinbelow:

Cereals (e.g. rice (Oryza sativa), barley (Hordeum vulgare), wheat(Triticum aestivum L.), rye (Secale cereale), oat (Avena), maize (Zeamays L.), kaoliang, etc.); legume (soybean, adzuki bean, fava bean,bean, peanut, etc.); fruit trees and fruits (apple, citrus fruits, pear,grapes, peach, plum, cherry, walnut, almond, banana, strawberry, etc.);vegetables (cabbage, tomato, spinach, broccoli, lettuce, onion, welshonion, green pepper, etc.); root vegetables (carrot, potato, sweetpotato, radish, lotus root, turnip, etc.); crop for processing (cotton,flax (Linum usitatissimum), paper mulberry (Broussonetia kasinoki SIEB),paperbush (Edgeworthia papyrifera), rape (Brassica napus L.), beet (Betavulgaris), hop, sugar cane (Saccharatum officinarum), sugar beet (Betavulgaris var. saccharifera), olive, rubber, coffee, tobacco, tea, etc.);gourd (pumpkin, cucumber, watermelon, melon, etc.); grass (orchardgrass, sorghum, timothy, clover, alfalfa, etc.); grass (Korean lawngrass, bent grass, etc.); crop for spicery (lavender (Lavandulaofficinalis CHAIX), rosemary, thyme, parsley, pepper, ginger, etc.); andflowers (chrysanthemum, rose, orchid, etc.).

Recently, gene recombinant crop (herbicide resistant crop, insect pestresistant crop incorporated with insecticidal toxin generating gene,disease resistant crop incorporated with disease resistance inducerproducing gene, taste improved crop, preservability improved crop, yieldimproved crop, etc.), insect sex pheromone (pheromone disruptingchemicals for leaf roller moths, cabbage armyworm, etc.), IPM(integrated pest management) technology using natural enemy insect havebeen progressed, and pesticide compositions of the present invention canbe used in combination with or by systematization with suchtechnologies.

The agrohorticultural agent of the present invention is generallyprepared into conveniently usable forms according to an ordinary mannerfor formulation of agrochemicals.

That is, the substituted pyrazolecarboxanilide derivative represented bythe formula (I) or salt of the present invention and, optionally, anadjuvant are blended with a suitable inert carrier in a properproportion and prepared into a suitable formulation form such as asuspension, emulsifiable concentrate, soluble concentrate, wettablepowder, water dispersible granule, granules, dust, tablets, pack or thelike through dissolution, dispersion, suspension, mixing, impregnation,adsorption or sticking.

The inert carrier usable in the present invention may be either solid orliquid. As a material usable as the solid carrier, there can beexemplified soybean flour, cereal flour, wood flour, bark flour, sawdust, powdered tobacco stalks, powdered walnut shells, bran, powderedcellulose, extraction residue of vegetables, resins such as powderedsynthetic polymers and the like, clays (e.g. kaolin, bentonite, and acidclay), talcs (e.g. talc and pyrophyllite), silica powders or flakes(e.g. diatomaceous earth, silica sand, mica and white carbon [synthetic,high-dispersion silicic acid, also called finely divided hydrated silicaor hydrated silicic acid, some of commercially available productscontain calcium silicate as the major component]), inorganic or mineralpowders such as activated carbon, powdered sulfur, pumice, calcineddiatomaceous earth, ground brick, fly ash, sand, calcium carbonate,calcium phosphate and the like, plastic carriers such as polyethylene,polypropylene, poly(vinylidene chloride) and the like, chemicalfertilizers (e.g. ammonium sulfate, ammonium phosphate, ammoniumnitrate, urea and ammonium chloride), and compost. These carriers may beused alone or as a mixture of two or more kinds thereof.

A material usable as the liquid carrier is selected from materials thathave solubility in themselves or which, even without such solubility,are capable of dispersing an active ingredient with the aid of anadjuvant. The following are typical examples of the liquid carrier andcan be used alone or as a mixture of two or more kinds thereof: water,alcohols (e.g. methanol, ethanol, isopropanol, butanol and ethyleneglycol), ketones (e.g. acetone, methyl ethyl ketone, methyl isobutylketone, diisobutyl ketone and cyclohexanone), ethers (e.g. ethyl ether,dioxane, Cellosolve, dipropyl ether and tetrahydrofuran), aliphatichydrocarbons (e.g. kerosene and mineral oils), aromatic hydrocarbons(e.g. benzene, toluene, xylene, solvent naphtha and alkylnaphthalenes),halogenated hydrocarbons (e.g. dichloroethane, chloroform, carbontetrachloride and chlorobenzene), esters (e.g. ethyl acetate,diisopropyl phthalate, dibutyl phthalate and dioctyl phthalate), amides(e.g. dimethylformamide, diethylformamide and dimethylacetamide),nitriles (e.g. acetonitrile), and dimethyl sulfoxide.

The following are typical examples of the adjuvant, which are useddepending upon purposes and used alone or in combination of two or morekinds, or in some cases, need not be used at all.

To emulsify, disperse, dissolve and/or wet a compound as activeingredient, a surfactant is used. As the surfactant, there can beexemplified polyoxyethylene alkyl ethers, polyoxyethylene alkylarylethers, polyoxyethylene higher fatty acid esters, polyoxyethyleneresonates, polyoxyethylene sorbitan monolaurate, polyoxyethylenesorbitan monooleate, alkylarylsulfonates, naphthalene sulfonic acidcondensation products, ligninsulfonates and higher alcohol sulfateesters.

Further, to stabilize the dispersion of a compound as active ingredient,tackify it and/or bind it, the adjuvants exemplified below may also beused, namely, there may also be used adjuvants such as casein, gelatin,starch, methyl cellulose, carboxymethyl cellulose, gum arabic,poly(vinyl alcohol)s, turpentine, bran oil, bentonite andligninsulfonates.

To improve the flowability of a solid product, the following adjuvantsmay also be used, namely, there may be used adjuvants such as waxes,stearates, alkyl phosphates, etc.

Adjuvants such as naphthalenesulfonic acid condensation products andpolycondensates of phosphates may be used as a peptizer for dispersibleproducts

Adjuvants such as silicone oils may also be used as a defoaming agent.

Adjuvants such as 1,2-benzisothiazoline-3-one, p-chloro-m-xylenol, butylp-hydroxybenzoate may also be added as a preservative.

Further, if necessary, functional spreading agents, active enhancerssuch as metabolic decomposition inhibitor like piperonyl butoxide,anti-freezing agents such as propylene glycol, antioxidants such as BHT,ultraviolet absorbers, and the other additives may also be added.

The content of the compound as active ingredient may be varied asrequired, and the compound as active ingredient may be used in aproportion properly chosen in the range of 0.01 to 90 parts by weightper 100 parts of the agrohorticultural agents. For example, in dusts orgranules, the suitable content of the compound as active ingredient isfrom 0.01 to 50% by weight. In emulsifiable concentrate or wettablepowders, it is also from 0.01 to 50% by weight.

The agrohorticultural agent of the present invention is used to controla variety of insect pests in the following manner: it is applied to acrop on which the insect pests are expected to appear, or a site whereappearance or growth of the insect pests is undesirable, as it is orafter being properly diluted with or suspended in water or the like, inan amount effective for control of the insect pests.

The applying dosage of the agrohorticultural agent of the presentinvention is varied depending upon various factors such as a purpose,insect pests to be controlled, a growth state of a plant, tendency ofinsect pests appearance, weather, environmental conditions, aformulation form, an application method, an application site andapplication time. It may be properly chosen in the range of 0.001 g to10 kg, preferably 0.01 g to 1 kg, (in terms of the compound as activeingredient) per 10 acres depending upon purposes.

The agrohorticultural agent of the present invention may be used inadmixture with other agrohorticultural insecticides, acaricides,nematocides, fungicides, biotic pesticides or the like in order toexpand both spectrum of controllable insect pest species and the periodof time when effective application are possible or to reduce the dosage.Furthermore, the agrohorticultural insecticide of the present inventionmay be used in admixture with herbicides, plant growth regulators,fertilizers or the like, depending upon application situations.

As the other agrohorticultural insecticides, acaricides and nematocides,which are used for the above purpose, there can be exemplifiedagrohorticultural insecticides, acaricides and nematocides, such asEthion, Trichlorfon, Metamidophos, Acephate, Dichlorvos, Mevinphos,Monocrotophos, Malathion, Dimethoate, Formothion, Mecarbam, Vamidothion,Thiometon, Disulfoton, Oxydeprofos, Naled, Methylparathion,Fenitrothion, Cyanophos, Propaphos, Fenthion, Prothiofos, Profenofos,Isofenphos, Temephos, Phenthoate, Dimethylvinphos, Chlorfenvinphos,Tetrachlorvinphos, Phoxim, Isoxathion, Pyraclofos, Methidathion,Chlorpyrifos, Chlorpyrifos-methyl, Pyridaphenthion, Diazinon,Pirimiphosmethyl, Phosalone, Phosmet, Dioxabenzophos, Quinalphos,Terbuphos, Ethoprophos, Cadusafos, Mesulfenfos, Spirodiclofen,Metaflumizone, Flubendiamide, DPS (NK-0795), Phosphocarb, Fenamiphos,Isoamidophos, Fosthiazate, Isazophos, Ethoprophos, Fenthion, Fostietane,Dichlofenthion, Thionazin, Sulprofos, Fensulfothion, Diamidafos,Pyrethrin, Allethrin, Prallethrin, Resmethrin, Permethrin, Tefluthrin,Bifenthrin, Fenpropathrin, Cypermethrin, α-Cypermethrin, Cyhalothrin,λ-Cyhalothrin, Deltamethrin, Acrinathrin, Fenvalerate, Esfenvalerate,Cycloprothrin, Ethofenprox, Halfenprox, Silafluofen, Flucythrinate,Fluvalinate, Methomyl, Oxamyl, Thiodicarb, Aldicarb, Alanycarb, Cartap,Metolcarb, Xylylcarb, Propoxur, Phenoxycarb, Fenobucarb, Ethiophencarb,Fenothiocarb, Bifenazate, BPMC, Carbaryl, Pirimicarb, Carbofuran,Carbosulfan, Furathiocarb, Benfuracarb, Aldoxycarb, Diafenthiuron,Diflubenzuron, Teflubenzuron, Hexaflumuron, Novaluron, Lufenuron,Flufenoxuron, Chlorfluazuron, Fenbutatin oxide, Tricyclohexyltinhydroxide, Sodium oleate, Potassium oleate, Methoprene, Hydroprene,Binapacryl, Amitraz, Dicofol, Kersen, Chlorobenzilate, Bromopropylate,Tetradifon, Bensultap, Benzoximate, Tebufenozide, Methoxyfenozide,Pyridalyl, Chromafenozide, Propargite, Acequinosyl, Endosulfan,Diofenolan, Chlorfenapyl, Fenpyroximate, Tolfenpyrad, Fipronil,Tebufenpyrad, Triazamate, Etoxazole, Hexythiazox, Nicotine sulfate,Nitenpyram, Acetamiprid, Thiacloprid, Imidacloprid, Thiamethoxam,Clothianidin, Dinotefuran, Fluazinam, Pyriproxyfen, Hydramethylnon,Pyrimidifen, Pyridaben, Cyromazine, TPIC (tripropyl isocyanurate),Pymetrozin, Clofentezin, Buprofedin, Thiocyclam, Fenazaquin,Chinomethionate, Indoxacarb, Polynactin complexes, Milbemectin,Abamectin, Emamectin-benzoate, Spinosad, BT (Bacillus thuringiensis),Azadirachtin, Rotenone, Hydroxypropyl starch, Levamisole hydrochloride,Metam-sodium, Morantel tartrate, Dazomet, Trichlamide, Pasteuriapenetrans, Monacrosporium-phymatophagum, etc.

As the agrohorticultural fungicides used for the same purpose as above,there can be exemplified agrohorticultural fungicides such as Sulfur,Lime sulfur, Copper sulfate basic, Iprobenfos, Edifenfos,Tolclofos-methyl, Thiram, Polycarbamate, Zineb, Maneb, Mancozeb,Propineb, Thiophanate, Thiophanate methyl, Benomyl, Iminoctadin acetate,Iminocutadin albecylate, Mepronil, Flutolanil, Pencycuron, Furametpyl,Thifluzamide, Metalaxyl, Oxadixyl, Carpropamid, Dichlofluanid,Flusulfamide, Chlorothalonil, Kresoxim-methyl, Fenoxanil, Himexazol,Etridiazol, Fluoroimide, Procymidone, Vinclozolin, Iprodione,Triadimefon, Bitertanol, Triflumizole, Ipconazole, Fluconazole,Propiconazole, Diphenoconazole, Myclobutanil, Tetraconazole,Hexaconazole, Tebuconazole, Thiadinil, Imibenconazole, Prochloraz,Pefurazoate, Cyproconazole, Isoprothiolane, Fenarimol, Pyrimetanil,Mepanipyrim, Pyrifenox, Fluazinam, Triforine, Diclomezine, Azoxystrobin,Thiadiazin, Captan, Probenazole, Acibenzolar-S-methyl, Fthalide,Tricyclazole, Pyroquilon, Chinomethionat, Oxolinic acid, Dithianon,Kasugamycin, Validamycin, Polyoxin, Blasticidin, Streptomycin, etc.

Similarly, as the herbicides, there can be exemplified herbicides suchas Glyphosate, Sulfosate, Glyfosinate, Bialaphos, Butamifos, Esprocarb,Prosulcarb, Benthiocarb, Pyributycarb, Asulam, Linuron, Dymron, Isouron,Bensulfuron methyl, Cyclosulfamuron, Cinosulfuron, Pyrazosulfuron ethyl,Azimsulfuron, Imazosulfuron, Tenylchlor, Alachlor, Pretilachlor,Clomeprop, Etobenzanid, Mefenacet, Pendimethalin, Bifenox, Acifluorfen,Lactfen, Cyhalofop-butyl, Ioxynil, Bromobutide, Alloxydim, Setoxydim,Napropamide, Indanofan, Pyrazolate, Benzofenap, Pyraflufen-ethyl,Imazapyl, Sulfentrazone, Cafenstrole, Bentoxazon, Oxadiazon, Paraquat,Diquat, Pyriminobac, Simazine, Atrazine, Dimethametryn, Triazyflam,Benflesate, Flutiacet-methyl, Quizalofop-ethyl, Bentazon, Calciumperoxide, etc.

As to the biotic pesticides, the same effect as above can be expected byusing the agrohorticultural agent of the present invention in admixturewith, for example, viral formulations obtained from nuclear polyhedrosisvirus (NPV), granulosis virus (GV), cytoplasmic polyhedrosis virus(CPV), entomopox virus (EPV), etc.; microbial pesticides utilized asinsecticides or nematicides, such as Monacrosporium phymatophagum,Steinernema carpocapsae, Steinernema kushidai, Pasteuria penetrans,etc.; microbial pesticides utilized as fungicides, such as Trichodermalignorum, Agrobacterium radiobactor, nonpathogenic Erwinia carotovora,Bacillus subtilis, etc.; and biotic pesticides utilized as herbicides,such as Xanthomonas campestris, etc.

In addition, the agrohorticultural agent of the present invention can beused in combination with biotic pesticides including natural enemiessuch as Parasitic wasp (Encarsia formosa), Parasitic wasp (Aphidiuscolemani), Gall-mildge (Aphidoletes aphidimyza), Parasitic wasp(Diglyphus isaea), Parasitic mite (Dacnusa sibirica), Predatory mite(Phytoseiulus persimilis), Predatory mite (Amblyseius cucumeris),Predatory bug (Orius sauteri), etc.; microbial pesticides such asBeauveria brongniartii, etc.; and pheromones such as (Z)-10-tetradecenylacetate, (E,Z)-4,10-tetradecadienyl acetate, (Z)-8-dodecenyl acetate,(Z)-11-tetradecenyl acetate, (Z)-13-icosen-10-one, (Z)-8-dodecenylacetate, (Z)-11-tetradecenyl acetate, (Z)-13-icosen-10-one,14-methyl-1-octadecene, etc.

EXAMPLES

The substituted pyrazolecarboxanilide derivatives represented by theformula (I), and substituted aniline derivative represented by theformula (II) and substituted pyrazolecarboxic acid represented by theformula (IV), which are intermediates therefore, of the presentinvention, are explained in the following by referring to Examples,which are not to be construed as limitative.

Example 1 Production of1,3-dimethyl-5-trifluoromethylpyrazole-4-carboxylic Acid (Compound No.4-1)

4-Iodo-1,3-dimethyl-5-trifluoromethylpyrazole (8.7 g, 30 mmol) wasdissolved in tetrahydrofuran (87 ml), and a solution (1.6 M, 28 ml) ofn-butyl lithium in hexane was slowly added under an argon atmospherewith cooling with dryice-acetone (not higher than −60° C.). Afterstirring at −70° C. for 30 min, the mixture was gradually warmed to roomtemperature while blowing in carbon dioxide. The reaction mixture waspoured into water, the organic layer was removed, and the aqueous layerwas acidified with hydrochloric acid. The aqueous layer was extractedwith ethyl acetate. The organic layer was washed with water, dried overmagnesium sulfate and concentrated under reduced pressure. The obtainedcrude crystals were washed with hexane to give the desired compound(4.67 g) as crystals.

yield 74%

Property: melting point 124-125.5° C.

Example 2 Production ofN-{3-isobutyl-4-[1-methoxy-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]phenyl}-1,5-dimethyl-3-trifluoromethylpyrazole-4-carboxamide(Compound No. 1-211)

1,5-Dimethyl-3-trifluoromethylpyrazole-4-carboxylic acid (2.09 g, 10mmol) was dissolved in thionyl chloride, and the mixture was heatedunder reflux for 3 hr. The mixture was concentrated under reducedpressure to give 1,5-dimethyl-3-trifluoromethylpyrazole-4-carbonylchloride. This was added to a solution of3-isobutyl-4-[1-methoxy-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]aniline(3.29 g, 10 mmol) and triethylamine (3.03 g, 30 mmol) in tetrahydrofuran(30 ml), and the mixture was heated under reflux for 2 hr. The reactionmixture was diluted with ethyl acetate, washed with water, and driedover magnesium sulfate. After concentration under reduced pressure, theobtained residue was purified by silica gel column chromatography(hexane:ethyl acetate=1:1) to give the desired compound (3.64 g) ascrystals.

yield 70%

Property: melting point 138-139° C.

Example 3 Production ofN-methoxymethyl-N-{3-isobutyl-4-[1-methoxy-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]phenyl}-1,5-dimethyl-3-trifluoromethylpyrazole-4-carboxamide(Compound No. 1-222)

Sodium hydride (32 mg, 60%, 0.8 mmol) was suspended in tetrahydrofuran(10 ml), and a solution ofN-{3-isobutyl-4-[1-methoxy-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]phenyl}-1,5-dimethyl-3-trifluoromethylpyrazole-4-carboxamide(250 mg, 0.48 mmol) in tetrahydrofuran (5 ml) was added dropwise. Afterstirring at room temperature for 30 min, a solution of chloromethylmethyl ether (64 mg, 0.8 mmol) in tetrahydrofuran (2 ml) was added andthe mixture was stirred for 5 hr. The reaction mixture was poured intodiluted hydrochloric acid and extracted with ethyl acetate. The organiclayer was washed with water, dried over magnesium sulfate, andconcentrated under reduced pressure, and the obtained residue waspurified by silica gel column chromatography (hexane:ethyl acetate=2:1)to give the desired compound (238 mg).

yield: 88%

Property: n_(D)1.4669 (22.4° C.)

Example 4 Production of2-methyl-5-n-propyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]aniline(Compound No. 3-1)

5-n-Propyl-2-methylaniline (14.9 g, 0.1 mol) was diluted in a mixedsolvent (300 ml) of tert-butyl methyl ether-water (1:1), andheptafluoroisopropyl iodide (29.6 g, 0.1 mol), tetrabutylammoniumhydrogen sulfate (3.4 g, 0.01 mol), sodium hydrogen carbonate (8.4 g,0.1 mol) and sodium dithionite (17 g, 0.1 mol) were successively added.The mixture was stirred overnight at room temperature. The reactionmixture was diluted in hexane, washed twice with 3N hydrochloric acid,and washed with aqueous sodium hydrogen carbonate and saturated brine.The organic layer was dried over magnesium sulfate, and concentratedunder reduced pressure. The residue was purified by silica gelchromatography (hexane:ethyl acetate 5:1) to give the desired compound(28.5 g).

yield: 90%

Property: ¹H-NMR [CDCl₃/TMS, δ value (ppm)] 7.09 (s, 1H), 6.54 (s, 1H),3.76 (bs, 2H), 2.63 (m, 2H), 2.13 (s, 3H), 1.58 (m, 2H), 0.96 (t, 3H)

Example 5 Production of4-[1-methoxy-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]-2-methyl-5-n-propylaniline(Compound No. 3-3)

2-Methyl-5-n-propyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]aniline(1.6 g, 5 mmol) was dissolved in a 28% solution (9.6 g) of sodiummethoxide in methanol, and the mixture was heated under reflux for 3 hr.After allowing to cool, the reaction mixture was poured into ice waterand extracted with ethyl acetate. The organic layer was washed withwater, dried over magnesium sulfate and concentrated under reducedpressure. The obtained residue was purified by silica gel columnchromatography (hexane:ethyl acetate=5:1) to give the desired compound(1.31 g).

yield: 79%

Property: ¹H-NMR [CDCl₃/TMS, δ value (ppm)] 7.10 (s, 1H), 6.66 (s, 1H),3.72 (bs, 2H), 3.42 (s, 3H), 2.84 (m, 2H), 2.14 (s, 3H), 1.61 (m, 2H),1.00 (t, 3H)

Example 6 Production of2-methyl-5-n-propyl-4-[2,2,2-trifluoro-1-(trifluoromethyl)ethyl]aniline(Compound No. 3-2)

2-Methyl-5-n-propyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]aniline(1.6 g, 5 mmol) was dissolved in dimethyl sulfoxide (20 ml), sodiumborohydride (378 mg, 10 mmol) was added by small portions, and themixture was stirred at 60° C. for 5 hr. Ice was added to the reactionmixture by small portions, and then acetic acid was added dropwise. Thereaction mixture was diluted with ethyl acetate, and the organic layerwas washed 4 times with water, dried over magnesium sulfate andconcentrated under reduced pressure to give the desired compound (1.47g).

yield: 99%

Property: ¹H-NMR [CDCl₃/TMS, δ value (ppm)] 7.18 (s, 1H), 6.54 (s, 1H),4.45-4.20 (br, 2H), 4.27 (m, 1H), 2.50 (dd, 2H), 2.14 (s, 3H), 1.57 (m,2H), 0.98 (t, 3H)

Example 7 Production ofN-{4-[1-methoxy-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]-2-methyl-5-n-propylphenyl}-1,3,5-trimethylpyrazole-4-carboxamide(compound No. 2-15)

1,3,5-Trimethylpyrazole-4-carbonyl chloride (172 mg, 1 mmol),4-[1-methoxy-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]-2-methyl-5-n-propylaniline(329 mg, 1 mmol) and triethylamine (303 mg, 3 mmol) were dissolved intetrahydrofuran (10 ml), and the mixture was heated under reflux for 3hr. The reaction mixture was diluted with ethyl acetate, and washed withwater. The organic layer was dried over anhydrous magnesium sulfate andconcentrated under reduced pressure. The obtained residue was purifiedby silica gel column chromatography (hexane:ethyl acetate=1:2) to givethe desired compound (360 mg).

yield: 77%

Property: melting point 132-134° C.

Example 8 Production ofN-acetyl-N-{4-[1-methoxy-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]-2-methyl-5-n-propylphenyl}-1,3,5-trimethylpyrazole-4-carboxamide(Compound No. 2-16)

Sodium hydride (32 mg, 60%, 0.8 mmol) was suspended in tetrahydrofuran(10 ml), and a solution ofN-{4-[1-methoxy-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]-2-methyl-5-n-propylphenyl}-1,3,5-trimethylpyrazole-4-carboxamide(250 mg, 0.53 mmol) in tetrahydrofuran (5 ml) was added dropwise. Afterstirring at room temperature for 30 min, a solution of acetic anhydride(80 mg, 0.78 mmol) in tetrahydrofuran (2 ml) was added, and the mixturewas stirred for one day. The reaction mixture was poured into dilutedhydrochloric acid, and the mixture was extracted with ethyl acetate. Theorganic layer was washed with water, dried over magnesium sulfate andconcentrated under reduced pressure, and the obtained residue waspurified by silica gel column chromatography (hexane:ethyl acetate=1:3)to give the desired compound (139 mg).

yield: 52%

Property: n_(D)1.4905 (25.9° C.)

Example 9 Production ofN-{2-methyl-5-n-propyl-4-[2,2,2-trifluoro-1-(trifluoromethyl)ethyl]phenyl-2-methyl-5-n-propylphenyl}-1,3,5-trimethylpyrazole-4-carboxamide(Compound No. 2-13)

In the same manner as in Example 7 except that2-methyl-5-n-propyl-4-[2,2,2-trifluoro-1-(trifluoromethyl)ethyl]anilinewas used instead of4-[1-methoxy-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]-2-methyl-5-n-propylaniline,the reaction is carried out for 3 hr to give the desired compound.

yield: 66%

Property: melting point 128-131° C.

Example 10 Production ofN-{3-isobutyl-4-[1-methoxy-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]phenyl}-1,3,5-trimethylpyrazole-4-carboxamide(Compound No. 1-155)

1,3,5-trimethylpyrazole-4-carbonyl chloride (3.93 g, 22.8 mmol),3-isobutyl-4-[1-methoxy-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]aniline(5.0 g, 15.2 mmol), and triethylamine (3.07 g, 30.4 mmol) were dissolvedin tetrahydrofuran (100 ml), and the mixture was heated under reflux for5 hr. The reaction mixture was diluted with ethyl acetate, and washedwith water. The organic layer was dried over anhydrous magnesium sulfateand concentrated under reduced pressure. The obtained crude crystalswere washed with ether to give the desired compound (5.62 g).

yield: 80%

Property: melting point 189-190° C.

Example 11 Production ofN-ethoxymethyl-N-{3-isobutyl-4-[1-methoxy-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]phenyl}-1,3,5-trimethylpyrazole-4-carboxamide(Compound No. 1-145)

Sodium hydride (29 mg, 60%, 0.73 mmol) was suspended in tetrahydrofuran(10 ml), and a solution ofN-{3-isobutyl-4-[1-methoxy-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]phenyl}-1,3,5-trimethylpyrazole-4-carboxamide(260 mg, 0.48 mmol) in tetrahydrofuran (5 ml) was added dropwise. Afterstirring at room temperature for 30 min, a solution of chloromethylethyl ether (70 mg, 0.73 mmol) in tetrahydrofuran (2 ml) was added, andthe mixture was stirred for one day. The reaction mixture was pouredinto diluted hydrochloric acid, and the mixture was extracted with ethylacetate. The organic layer was washed with water, dried over magnesiumsulfate and concentrated under reduced pressure, and the obtainedresidue was purified by silica gel column chromatography (hexane:ethylacetate=1:3) to give the desired compound (200 mg).

yield: 69%

Property: n_(D)1.4892 (22.4° C.)

Example 12 Production ofN-isobutyloxycarbonyl-N-{3-isobutyl-4-[1-methoxy-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]phenyl}-1,3,5-trimethylpyrazole-4-carboxamide(Compound No. 1-152)

Sodium hydride (29 mg, 60%, 0.73 mmol) was suspended in tetrahydrofuran(10 ml), and a solution ofN-{3-isobutyl-4-[1-methoxy-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]phenyl}-1,3,5-trimethylpyrazole-4-carboxamide(260 mg, 0.48 mmol) in tetrahydrofuran (5 ml) was added dropwise. Afterstirring at room temperature for 30 min, a solution of isobutylchlorocarbonate (100 mg, 0.73 mmol) in tetrahydrofuran (2 ml) was added,and the mixture was stirred for one day. The reaction mixture was pouredinto diluted hydrochloric acid and extracted with ethyl acetate. Theorganic layer was washed with water, dried over magnesium sulfate andconcentrated under reduced pressure, and the obtained residue waspurified by silica gel column chromatography (hexane:ethyl acetate=1:1)to give the desired compound (280 mg).

yield: 91%

Property: n_(D)1.4829 (22.3° C.)

Example 13 Production ofN-{3-isobutyl-4-[2,2,2-trifluoro-1-(trifluoromethyl)ethyl]phenyl}-1,3,5-trimethylpyrazole-4-carboxamide(Compound No. 1-123)

1,3,5-Trimethylpyrazole-4-carbonyl chloride (2.09 g, 10.0 mmol),3-isobutyl-4-[2,2,2-trifluoro-1-(trifluoromethyl)ethyl]aniline (2.0 g,6.69 mmol), and triethylamine (1.35 g, 13.4 mmol) were dissolved intetrahydrofuran (60 ml), and the mixture was heated under reflux for 5hr. The reaction mixture was diluted with ethyl acetate, and washed withwater. The organic layer was dried over anhydrous magnesium sulfate andconcentrated under reduced pressure, and the obtained residue waspurified by silica gel column chromatography (hexane:ethyl acetate=1:3)to give the desired compound (2.41 g).

yield: 77%

Property: melting point 148-151° C.

Example 14 Production ofN-acetyl-N-{3-isobutyl-4-[2,2,2-trifluoro-1-(trifluoromethyl)ethyl]phenyl}-1,3,5-trimethylpyrazole-4-carboxamide(Compound No. 1-125)

Sodium hydride (38 mg, 60%, 0.96 mmol) was suspended in tetrahydrofuran(10 ml), and a solution ofN-{3-isobutyl-4-[2,2,2-trifluoro-1-(trifluoromethyl)ethyl]phenyl}-1,3,5-trimethylpyrazole-4-carboxamide(300 mg, 0.64 mmol) in tetrahydrofuran (5 ml) was added dropwise. Afterstirring at room temperature for 30 min, a solution of acetyl chloride(75 mg, 0.96 mmol) in tetrahydrofuran (2 ml) was added, and the mixturewas stirred for one day. The reaction mixture was poured into dilutedhydrochloric acid and extracted with ethyl acetate. The organic layerwas washed with water, dried over magnesium sulfate and concentratedunder reduced pressure, and the obtained residue was purified by silicagel column chromatography (hexane:ethyl acetate=1:3) to give the desiredcompound (90 mg).

yield: 28%

Property: n_(D)1.5021 (22.5° C.)

Reference Example Production of 14-iodo-1,3-dimethyl-5-trifluoromethylpyrazole

Iodine (30 g) was dissolved in 60% sulfuric acid (fuming, 80 g), and1,3-dimethyl-5-trifluoromethylpyrazole (13.12 g, 80 mmol) was slowlyadded under ice-cooling. The mixture was stirred at 0° C. for 2 hr. Thereaction mixture was poured into ice water and extracted with ethylacetate. The organic layer was washed with aqueous sodium thiosulfateand saturated brine, dried over magnesium sulfate and concentrated underreduced pressure. The obtained crude crystals were washed with hexane togive the desired compound (20 g) as crystals.

yield 86%

Property: ¹H-NMR [CDCl₃/TMS, δ value (ppm)] 3.98 (s, 3H), 2.26 (s, 3H)

Typical formulation examples and test example of the present inventionare described below but they should not be construed as limiting thescope of the invention.

As used in the examples, the terms “part” and “parts” are by weight.

Formulation Example 1

Each compound listed in Table 1 or Table 2 10 parts Xylene 70 partsN-methylpyrrolidone 10 parts Mixture of polyoxyethylene nonylphenyl 10parts ether and calcium alkylbenzenesulfonate

An emulsifiable concentrate was prepared by mixing uniformly the aboveingredients to effect dissolution.

Formulation Example 2

Each compound listed in Table 1 or Table 2  3 parts Clay powder 82 partsDiatomaceous earth powder 15 parts

A dust was prepared by mixing uniformly and grinding the aboveingredients.

Formulation Example 3

Each compound listed in Table 1 or Table 2 5 parts Mixed powder ofbentonite and clay 90 parts  Calcium ligninsulfonate 5 parts

Granules were prepared by mixing the above ingredients uniformly, andkneading the resulting mixture together with a suitable amount of water,followed by granulation and drying.

Formulation Example 4

Each compound listed in Table 1 or Table 2 20 parts Mixture of kaolinand synthetic 75 parts high-dispersion silicic acid Mixture ofpolyoxyethylene nonylphenyl  5 parts ether and calciumalkylbenzenesulfonate

A wettable powder was prepared by mixing uniformly and grinding theabove ingredients.

Test Example 1 Acaricidal Action on Two-Spotted Spider Mite (Tetranychusurticae)

Kidney bean leaf disk with a diameter of 2 cm was placed on the wettedfilter paper. Ten adult females of two-spotted spider mite wereinoculated on each leaf disk, and were sprayed with 50 ml of testsolution, prepared by diluting a formulation containing each compoundlisted in Table 1 or Table 2 as an active ingredient to adjust each ofthe concentrations to 500 ppm, 50 ppm and 5 ppm. Two days after thetreatment, the survived mites were counted. The corrected mortality wascalculated by the following equation and the acaricidal activity wasjudged according to the criterion shown below. The experiment wascarried out with two replicates under the condition at 25° C.

${{Corrected}\mspace{14mu} {mortality}\mspace{14mu} (\%)} = {\frac{\begin{matrix}{{{Number}\mspace{14mu} {of}\mspace{14mu} {survived}\mspace{14mu} {mites}\mspace{14mu} {in}\mspace{14mu} {untreated}\mspace{14mu} {group}} -} \\{{Number}\mspace{14mu} {of}\mspace{14mu} {survived}\mspace{14mu} {mites}\mspace{14mu} {in}\mspace{14mu} {treated}\mspace{14mu} {group}}\end{matrix}}{{Number}\mspace{14mu} {of}\mspace{14mu} {survived}\mspace{14mu} {mites}\mspace{14mu} {in}\mspace{14mu} {untreated}\mspace{14mu} {group}} \times 100}$

Criterion:

A—Corrected mortality 100%

B—Corrected mortality 99%-90%

C—Corrected mortality 89%-80%

D—Corrected mortality 79%-50%

As comparative compounds, compound Nos. 1-163 and 1-164 disclosed inJP-A-2003-48878 were used.

As a result of the above-mentioned test, the compound Nos. 1-1, 1-3,1-4, 1-6, 1-8, 1-10, 1-12, 1-13, 1-15, 1-16, 1-25 to 1-28, 1-31, 1-34 to1-37, 1-45, 1-47 to 1-49, 1-51 to 54, 1-56, 1-57, 1-59, 1-67, 1-69 to1-72, 1-74 to 1-76, 1-89, 1-101 to 1-114, 1-120 to 1-160, 1-176 to1-225, 1-228, 1-234, 1-246, 1-258, 1-260, 1-266, 1-270, 1-282, 1-285,1-294, 1-306 to 1-325, 1-327 to 1-332, 1-335 to 1-337, 1-339 to 1-342,1-344 to 1-358, 1-361 to 1-373, 1-375 to 1-380, 1-382 to 1-384, 1-386 to1-389, 1-391 to 1-394, 1-396, 1-399 to 1-406, 1-412 to 416, 1-420 to1-423, 1-425 to 1-427, 1-429 to 1-433, 1-435 to 1-439, 1-441 to 1-445,1-448, 1-450 to 1-452, 1-454 to 1-463, 1-467 to 1-470, 1-473, 1-477,1-478, 1-482 to 1-487, 1-489 to 1-493, 1-496 to 1-502, 1-510, 1-514,1-515, 1-518, 1-519, 1-523 to 1-527, 1-531, 1-539 to 1-541, 1-546 to1-549, 2-13, 2-15 to 2-17, 2-21 to 2-23, 2-25, 2-34, 2-36 to 39, 2-41 to43 and 2-45 of the present invention showed A activity at anyconcentration of 500 ppm, 50 ppm and 5 ppm, and the compound Nos. 1-23,1-32, 1-78, 1-173, 1-284, 1-326, 1-334, 1-338, 1-343, 1-385, 1-397 to1-398, 1-408, 1-410, 1-417, 1-440, 1-447, 1-449, 1-464, 1-472, 1-475,1-476, 1-479, 1-480, 1-504 to 1-506, 1-509, 1-521, 1-529, 1-530, 1-533,1-542, 2-26 to 2-33, 2-40 and 2-46 showed A activity at anyconcentration of 500 ppm and 50 ppm. In contrast, the both controlcompounds did not show an acaricide activity even at the concentrationof 500 ppm.

INDUSTRIAL APPLICABILITY

According to the present invention, agrohorticultural agents,particularly insecticides and acaricides, having superior properties ascompared to conventional techniques can be provided.

This application is based on patent application Nos. 234405/2005,322531/2005 and 114937/2006 filed in Japan, the contents of which arehereby incorporated by reference.

While this invention has been shown and described with references topreferred embodiments thereof, it will be understood by those skilled inthe art that various changes in form and details may be made thereinwithout departing from the scope of the invention encompassed by theappended claims.

All patents, patent publications and other publications identified orreferenced herein are incorporated by reference in their entirety.

1. A substituted pyrazolecarboxanilide derivative represented by theformula (I):

wherein R¹ is 1a) a hydrogen atom, 2a) a C₁-C₈ alkyl group, 3a) a haloC₁-C₆ alkyl group, 4a) a C₁-C₆ alkylcarbonyl group, 5a) a halo C₁-C₆alkylcarbonyl group, 6a) a C₂-C₆ alkenylcarbonyl group, 7a) a halo C₂-C₆alkenylcarbonyl group, 8a) a C₁-C₆ alkylcarbonyl C₁-C₆ alkyl group, 9a)a C₃-C₆ cycloalkyl group, 10a) a halo C₃-C₆ cycloalkyl group, 11a) aC₃-C₆ cycloalkyl C₁-C₆ alkyl group, 12a) a halo C₃-C₆ cycloalkyl C₁-C₆alkyl group, 13a) a C₂-C₆ alkenyl group, 14a) a halo C₂-C₆ alkenylgroup, 15a) a C₂-C₆ alkynyl group, 16a) a halo C₂-C₆ alkynyl group, 17a)a C₁-C₁₀ alkoxy C₁-C₆ alkyl group, 18a) a halo C₁-C₆ alkoxy C₁-C₆ alkylgroup, 19a) a C₂-C₆ alkenyloxy C₁-C₆ alkyl group, 20a) a C₁-C₆ alkoxyC₁-C₆ alkoxy C₁-C₆ alkyl group, 21a) a C₁-C₆ alkylthio C₁-C₆ alkylgroup, 22a) a halo C₁-C₆ alkylthio C₁-C₆ alkyl group, 23a) a C₁-C₆alkylsulfinyl C₁-C₆ alkyl group, 24a) a halo C₁-C₆ alkylsulfinyl C₁-C₆alkyl group, 25a) a C₁-C₆ alkylsulfonyl C₁-C₆ alkyl group, 26a) a haloC₁-C₆ alkylsulfonyl C₁-C₆ alkyl group, 27a) a mono C₁-C₆ alkylaminoC₁-C₆ alkyl group, 28a) a di C₁-C₆ alkylamino C₁-C₆ alkyl group whereinthe alkyl groups are the same or different, 29a) a phenyl C₁-C₆ alkoxyC₁-C₆ alkyl group, 30a) a substituted phenyl C₁-C₆ alkoxy C₁-C₆ alkylgroup having, on the ring, one or more, the same or differentsubstituents selected from a) a halogen atom, b) a cyano group, c) anitro group, d) a C₁-C₆ alkyl group, e) a halo C₁-C₆ alkyl group, f) aC₁-C₆ alkoxy group, g) a halo C₁-C₆ alkoxy group, h) a C₁-C₆ alkylthiogroup, i) a halo C₁-C₆ alkylthio group, j) a C₁-C₆ alkylsulfinyl group,k) a halo C₁-C₆ alkylsulfinyl group, l) a C₁-C₆ alkylsulfonyl group, m)a halo C₁-C₆ alkylsulfonyl group, n) a mono C₁-C₆ alkylamino group, o) adi C₁-C₆ alkylamino group wherein the alkyl groups are the same ordifferent, and p) a C₁-C₆ alkoxycarbonyl group, 31a) a C₁-C₁₆alkoxycarbonyl group, 32a) a C₁-C₆ alkoxy C₁-C₆ alkoxycarbonyl group,33a) a halo C₁-C₆ alkoxycarbonyl group, 34a) a C₂-C₆ alkenyloxycarbonylgroup, 35a) a C₁-C₆ alkylthiocarbonyl group, 36a) a mono C₁-C₆alkylaminocarbonyl group, 37a) a di C₁-C₆ alkylaminocarbonyl groupwherein the alkyl groups are the same or different, 38a) a C₁-C₆alkoxycarbonyl C₁-C₆ alkyl group, 39a) a C₁-C₆ alkylsulfonyl group, 40a)a halo C₁-C₆ alkylsulfonyl group, 41a) a cyano C₁-C₆ alkyl group, 42a) aphenyl C₁-C₆ alkyl group, 43a) a substituted phenyl C₁-C₆ alkyl grouphaving, on the ring, one or more, the same or different substituentsselected from a) a halogen atom, b) a cyano group, c) a nitro group, d)a C₁-C₆ alkyl group, e) a halo C₁-C₆ alkyl group, f) a C₁-C₆ alkoxygroup, g) a halo C₁-C₆ alkoxy group, h) a C₁-C₆ alkylthio group, i) ahalo C₁-C₆ alkylthio group, j) a C₁-C₆ alkylsulfinyl group, k) a haloC₁-C₆ alkylsulfinyl group, l) a C₁-C₆ alkylsulfonyl group, m) a haloC₁-C₆ alkylsulfonyl group, n) a mono C₁-C₆ alkylamino group, o) a diC₁-C₆ alkylamino group wherein the alkyl groups are the same ordifferent, and p) a C₁-C₆ alkoxycarbonyl group, 44a) a phenylcarbonylgroup, 45a) a substituted phenylcarbonyl group having, on the ring, oneor more, the same or different substituents selected from a) a halogenatom, b) a cyano group, c) a nitro group, d) a C₁-C₆ alkyl group, e) ahalo C₁-C₆ alkyl group, f) a C₁-C₆ alkoxy group, g) a halo C₁-C₆ alkoxygroup, h) a C₁-C₆ alkylthio group, i) a halo C₁-C₆ alkylthio group, j) aC₁-C₆ alkylsulfinyl group, k) a halo C₁-C₆ alkylsulfinyl group, l) aC₁-C₆ alkylsulfonyl group, m) a halo C₁-C₆ alkylsulfonyl group, n) amono C₁-C₆ alkylamino group, o) a di C₁-C₆ alkylamino group wherein thealkyl groups are the same or different, and p) a C₁-C₆ alkoxycarbonylgroup, 46a) a heterocyclylcarbonyl group, 47a) a substitutedheterocyclylcarbonyl group having, on the ring, one or more, the same ordifferent substituents selected from a) a halogen atom, b) a cyanogroup, c) a nitro group, d) a C₁-C₆ alkyl group, e) a halo C₁-C₆ alkylgroup, f) a C₁-C₆ alkoxy group, g) a halo C₁-C₆ alkoxy group, h) a C₁-C₆alkylthio group, i) a halo C₁-C₆ alkylthio group, j) a C₁-C₆alkylsulfinyl group, k) a halo C₁-C₆ alkylsulfinyl group, l) a C₁-C₆alkylsulfonyl group, m) a halo C₁-C₆ alkylsulfonyl group, n) a monoC₁-C₆ alkylamino group, o) a di C₁-C₆ alkylamino group wherein the alkylgroups are the same or different, and p) a C₁-C₆ alkoxycarbonyl group,48a) a phenoxycarbonyl group, 49a) a substituted phenoxycarbonyl grouphaving, on the ring, one or more, the same or different substituentsselected from a) a halogen atom, b) a cyano group, c) a nitro group, d)a C₁-C₆ alkyl group, e) a halo C₁-C₆ alkyl group, f) a C₁-C₆ alkoxygroup, g) a halo C₁-C₆ alkoxy group, h) a C₁-C₆ alkylthio group, i) ahalo C₁-C₆ alkylthio group, j) a C₁-C₆ alkylsulfinyl group, k) a haloC₁-C₆ alkylsulfinyl group, l) a C₁-C₆ alkylsulfonyl group, m) a haloC₁-C₆ alkylsulfonyl group, n) a mono C₁-C₆ alkylamino group, o) a diC₁-C₆ alkylamino group wherein the alkyl groups are the same ordifferent, and p) a C₁-C₆ alkoxycarbonyl group, 50a) a phenoxy C₁-C₆alkylcarbonyl group, 51a) a substituted phenoxy C₁-C₆ alkylcarbonylgroup having, on the ring, one or more, the same or differentsubstituents selected from a) a halogen atom, b) a cyano group, c) anitro group, d) a C₁-C₆ alkyl group, e) a halo C₁-C₆ alkyl group, f) aC₁-C₆ alkoxy group, g) a halo C₁-C₆ alkoxy group, h) a C₁-C₆ alkylthiogroup, i) a halo C₁-C₆ alkylthio group, j) a C₁-C₆ alkylsulfinyl group,k) a halo C₁-C₆ alkylsulfinyl group, l) a C₁-C₆ alkylsulfonyl group, m)a halo C₁-C₆ alkylsulfonyl group, n) a mono C₁-C₆ alkylamino group, o) adi C₁-C₆ alkylamino group wherein the alkyl groups are the same ordifferent, and p) a C₁-C₆ alkoxycarbonyl group, 52a) a phenylsulfonylgroup, 53a) a substituted phenylsulfonyl group having, on the ring, oneor more, the same or different substituents selected from a) a halogenatom, b) a cyano group, c) a nitro group, d) a C₁-C₆ alkyl group, e) ahalo C₁-C₆ alkyl group, f) a C₁-C₆ alkoxy group, g) a halo C₁-C₆ alkoxygroup, h) a C₁-C₆ alkylthio group, i) a halo C₁-C₆ alkylthio group, j) aC₁-C₆ alkylsulfinyl group, k) a halo C₁-C₆ alkylsulfinyl group, l) aC₁-C₆ alkylsulfonyl group, m) a halo C₁-C₆ alkylsulfonyl group, n) amono C₁-C₆ alkylamino group, o) a di C₁-C₆ alkylamino group wherein thealkyl groups are the same or different, and p) a C₁-C₆ alkoxycarbonylgroup, 54a) a di C₁-C₆ alkylphosphono group wherein the alkyl groups arethe same or different, 55a) a di C₁-C₆ alkylphosphonothio group whereinthe alkyl groups are the same or different, 56a) a N—C₁-C₆ alkyl-N—C₁-C₆alkoxycarbonylaminothio group, 57a) a N—C₁-C₆ alkyl-N—C₁-C₆alkoxycarbonyl C₁-C₆ alkylaminothio group, 58a) a di C₁-C₆alkylaminothio group wherein the alkyl groups are the same or different,59a) a C₃-C₆ cycloalkylcarbonyl group, 60a) a halo C₃-C₆cycloalkylcarbonyl group, 61a) a C₁-C₆ alkyl C₃-C₆ cycloalkylcarbonylgroup, 62a) a halo C₁-C₆ alkyl C₃-C₆ cycloalkylcarbonyl group, 63a) aphenyl C₁-C₆ alkylcarbonyl group, 64a) a substituted phenyl C₁-C₆alkylcarbonyl group having, on the ring, one or more, the same ordifferent substituents selected from a) a halogen atom, b) a cyanogroup, c) a nitro group, d) a C₁-C₆ alkyl group, e) a halo C₁-C₆ alkylgroup, f) a C₁-C₆ alkoxy group, g) a halo C₁-C₆ alkoxy group, h) a C₁-C₆alkylthio group, i) a halo C₁-C₆ alkylthio group, j) a C₁-C₆alkylsulfinyl group, k) a halo C₁-C₆ alkylsulfinyl group, l) a C₁-C₆alkylsulfonyl group, m) a halo C₁-C₆ alkylsulfonyl group, n) a monoC₁-C₆ alkylamino group, o) a di C₁-C₆ alkylamino group wherein the alkylgroups are the same or different, and p) a C₁-C₆ alkoxycarbonyl group,65a) a phenyl C₃-C₆ cycloalkylcarbonyl group, 66a) a substituted phenylC₃-C₆ cycloalkylcarbonyl group having, on the ring, one or more, thesame or different substituents selected from a) a halogen atom, b) acyano group, c) a nitro group, d) a C₁-C₆ alkyl group, e) a halo C₁-C₆alkyl group, f) a C₁-C₆ alkoxy group, g) a halo C₁-C₆ alkoxy group, h) aC₁-C₆ alkylthio group, i) a halo C₁-C₆ alkylthio group, j) a C₁-C₆alkylsulfinyl group, k) a halo C₁-C₆ alkylsulfinyl group, l) a C₁-C₆alkylsulfonyl group, m) a halo C₁-C₆ alkylsulfonyl group, n) a monoC₁-C₆ alkylamino group, o) a di C₁-C₆ alkylamino group wherein the alkylgroups are the same or different, and p) a C₁-C₆ alkoxycarbonyl group,67a) a C₃-C₆ cycloalkyl C₁-C₆ alkylcarbonyl group, 68a) a C₁-C₆ alkoxyC₁-C₆ alkylcarbonyl group, 69a) a halo C₃-C₆ cycloalkyl C₁-C₆alkylcarbonyl group, 70a) a phenoxy C₁-C₆ alkoxycarbonyl group, 71a) asubstituted phenoxy C₁-C₆ alkoxycarbonyl group having, on the ring, oneor more, the same or different substituents selected from a) a halogenatom, b) a cyano group, c) a nitro group, d) a C₁-C₆ alkyl group, e) ahalo C₁-C₆ alkyl group, f) a C₁-C₆ alkoxy group, g) a halo C₁-C₆ alkoxygroup, h) a C₁-C₆ alkylthio group, i) a halo C₁-C₆ alkylthio group, j) aC₁-C₆ alkylsulfinyl group, k) a halo C₁-C₆ alkylsulfinyl group, l) aC₁-C₆ alkylsulfonyl group, m) a halo C₁-C₆ alkylsulfonyl group, n) amono C₁-C₆ alkylamino group, o) a di C₁-C₆ alkylamino group wherein thealkyl groups are the same or different, and p) a C₁-C₆ alkoxycarbonylgroup, 72a) a C₁-C₆ alkylcarbonyloxy C₁-C₆ alkyl group, 73a) a C₁-C₆alkylcarbonyl C₁-C₆ alkylcarbonyl group, or 74a) a C₁-C₆ alkoxycarbonylC₁-C₆ alkylcarbonyl group; R² is 1b) a hydrogen atom, 2b) a halogenatom, 3b) a C₁-C₆ alkyl group, 4b) a halo C₁-C₆ alkyl group, 5b) a cyanogroup, 6b) a hydroxy group, 7b) a C₁-C₆ alkoxy group, 8b) a halo C₁-C₆alkoxy group, 9b) a C₁-C₆ alkoxy C₁-C₃ alkoxy group, 10b) a halo C₁-C₆alkoxy C₁-C₃ alkoxy group, 11b) a C₁-C₆ alkylthio C₁-C₃ alkoxy group,12b) a halo C₁-C₆ alkylthio C₁-C₃ alkoxy group, 13b) a C₁-C₆alkylsulfinyl C₁-C₃ alkoxy group, 14b) a halo C₁-C₆ alkylsulfinyl C₁-C₃alkoxy group, 15b) a C₁-C₆ alkylsulfonyl C₁-C₃ alkoxy group, 16b) a haloC₁-C₆ alkylsulfonyl C₁-C₃ alkoxy group, 17b) a mono C₁-C₆ alkylaminoC₁-C₃ alkoxy group, 18b) a di C₁-C₆ alkylamino C₁-C₃ alkoxy groupwherein the alkyl groups are the same or different, 19b) a C₁-C₆alkylthio group, 20b) a halo C₁-C₆ alkylthio group, 21b) a C₁-C₆alkylsulfinyl group, 22b) a halo C₁-C₆ alkylsulfinyl group, 23b) a C₁-C₆alkylsulfonyl group, 24b) a halo C₁-C₆ alkylsulfonyl group, 25b) anamino group, 26b) a mono C₁-C₆ alkylamino group, 27b) a di C₁-C₆alkylamino group wherein the alkyl groups are the same or different,28b) a phenoxy group, 29b) a substituted phenoxy group having, on thering, one or more, the same or different substituents selected from a) ahalogen atom, b) a cyano group, c) a nitro group, d) a C₁-C₆ alkylgroup, e) a halo C₁-C₆ alkyl group, f) a C₁-C₆ alkoxy group, g) a haloC₁-C₆ alkoxy group, h) a C₁-C₆ alkylthio group, i) a halo C₁-C₆alkylthio group, j) a C₁-C₆ alkylsulfinyl group, k) a halo C₁-C₆alkylsulfinyl group, l) a C₁-C₆ alkylsulfonyl group, m) a halo C₁-C₆alkylsulfonyl group, n) a mono C₁-C₆ alkylamino group, o) a di C₁-C₆alkylamino group wherein the alkyl groups are the same or different, andp) a C₁-C₆ alkoxycarbonyl group, 30b) a phenylthio group, 31b) asubstituted phenylthio group having, on the ring, one or more, the sameor different substituents selected from a) a halogen atom, b) a cyanogroup, c) a nitro group, d) a C₁-C₆ alkyl group, e) a halo C₁-C₆ alkylgroup, f) a C₁-C₆ alkoxy group, g) a halo C₁-C₆ alkoxy group, h) a C₁-C₆alkylthio group, i) a halo C₁-C₆ alkylthio group, j) a C₁-C₆alkylsulfinyl group, k) a halo C₁-C₆ alkylsulfinyl group, l) a C₁-C₆alkylsulfonyl group, m) a halo C₁-C₆ alkylsulfonyl group, n) a monoC₁-C₆ alkylamino group, o) a di C₁-C₆ alkylamino group wherein the alkylgroups are the same or different, and p) a C₁-C₆ alkoxycarbonyl group,32b) a phenylsulfinyl group, 33b) a substituted phenylsulfinyl grouphaving, on the ring, one or more, the same or different substituentsselected from a) a halogen atom, b) a cyano group, c) a nitro group, d)a C₁-C₆ alkyl group, e) a halo C₁-C₆ alkyl group, f) a C₁-C₆ alkoxygroup, g) a halo C₁-C₆ alkoxy group, h) a C₁-C₆ alkylthio group, i) ahalo C₁-C₆ alkylthio group, j) a C₁-C₆ alkylsulfinyl group, k) a haloC₁-C₆ alkylsulfinyl group, l) a C₁-C₆ alkylsulfonyl group, m) a haloC₁-C₆ alkylsulfonyl group, n) a mono C₁-C₆ alkylamino group, o) a diC₁-C₆ alkylamino group wherein the alkyl groups are the same ordifferent, and p) a C₁-C₆ alkoxycarbonyl group, 34b) a phenylsulfonylgroup, 35b) a substituted phenylsulfonyl group having, on the ring, oneor more, the same or different substituents selected from a) a halogenatom, b) a cyano group, c) a nitro group, d) a C₁-C₆ alkyl group, e) ahalo C₁-C₆ alkyl group, f) a C₁-C₆ alkoxy group, g) a halo C₁-C₆ alkoxygroup, h) a C₁-C₆ alkylthio group, i) a halo C₁-C₆ alkylthio group, j) aC₁-C₆ alkylsulfinyl group, k) a halo C₁-C₆ alkylsulfinyl group, l) aC₁-C₆ alkylsulfonyl group, m) a halo C₁-C₆ alkylsulfonyl group, n) amono C₁-C₆ alkylamino group, o) a di C₁-C₆ alkylamino group wherein thealkyl groups are the same or different, and p) a C₁-C₆ alkoxycarbonylgroup, 36b) a phenyl C₁-C₆ alkoxy group, or 37b) a substituted phenylC₁-C₆ alkoxy group having, on the ring, one or more, the same ordifferent substituents selected from a) a halogen atom, b) a cyanogroup, c) a nitro group, d) a C₁-C₆ alkyl group, e) a halo C₁-C₆ alkylgroup, f) a C₁-C₆ alkoxy group, g) a halo C₁-C₆ alkoxy group, h) a C₁-C₆alkylthio group, i) a halo C₁-C₆ alkylthio group, j) a C₁-C₆alkylsulfinyl group, k) a halo C₁-C₆ alkylsulfinyl group, l) a C₁-C₆alkylsulfonyl group, m) a halo C₁-C₆ alkylsulfonyl group, n) a monoC₁-C₆ alkylamino group, o) a di C₁-C₆ alkylamino group wherein the alkylgroups are the same or different, and p) a C₁-C₆ alkoxycarbonyl group; Gis 1c) a C₂-C₁₀ alkyl group, 2c) a halo C₂-C₁₀ alkyl group, 3c) a C₃-C₁₀alkenyl group, 4c) a halo C₃-C₁₀ alkenyl group, 5c) a C₃-C₁₀ alkynylgroup, 6c) a halo C₃-C₁₀ alkynyl group, 7c) a C₃-C₁₀ cycloalkyl group,8c) a substituted C₃-C₁₀ cycloalkyl group having, on the ring, one ormore, the same or different substituents selected from a) a halogenatom, b) a C₁-C₆ alkyl group, and c) a halo C₁-C₆ alkyl group, 9c) aC₃-C₁₀ cycloalkenyl group, 10c) a substituted C₃-C₁₀ cycloalkenyl grouphaving, on the ring, one or more, the same or different substituentsselected from a) a halogen atom, b) a C₁-C₆ alkyl group, and c) a haloC₁-C₆ alkyl group, 11c) a C₃-C₈ cycloalkyl C₁-C₆ alkyl group, or 12c) ahalo C₃-C₈ cycloalkyl C₁-C₆ alkyl group; Z is an oxygen atom or a sulfuratom; X may be the same or different and is 1d) a hydrogen atom, 2d) ahalogen atom, 3d) a cyano group, 4d) a nitro group, 5d) a C₁-C₆ alkylgroup, or 6d) a halo C₁-C₆ alkyl group; Y¹ is 1e) a hydrogen atom, 2e) aC₁-C₆ alkyl group, 3e) a halo C₁-C₆ alkyl group, 4e) a C₂-C₆ alkenylgroup, 5e) a halo C₂-C₆ alkenyl group, 6e) a C₂-C₆ alkynyl group, 7e) ahalo C₂-C₆ alkynyl group, 8e) a C₁-C₆ alkoxy C₁-C₆ alkoxy C₁-C₆ alkylgroup, 9e) a hydroxy C₁-C₆ alkyl group, 10e) a C₁-C₆ alkylcarbonyloxyC₁-C₆ alkyl group, 11e) a C₃-C₆ cycloalkyl group, 12e) a halo C₃-C₆cycloalkyl group, 13e) a C₃-C₆ cycloalkyl C₁-C₆ alkyl group, 14e) a haloC₃-C₆ cycloalkyl C₁-C₆ alkyl group, 15e) a C₁-C₆ alkylsulfonyl group,16e) a halo C₁-C₆ alkylsulfonyl group, 17e) a C₁-C₆ alkylthio C₁-C₆alkyl group, 18e) a halo C₁-C₆ alkylthio C₁-C₆ alkyl group, 19e) a C₁-C₆alkylsulfinyl C₁-C₆ alkyl group, 20e) a halo C₁-C₆ alkylsulfinyl C₁-C₆alkyl group, 21e) a C₁-C₆ alkylsulfonyl C₁-C₆ alkyl group, 22e) a haloC₁-C₆ alkylsulfonyl C₁-C₆ alkyl group, 23e) a mono C₁-C₆ alkylaminoC₁-C₆ alkyl group, 24e) a di C₁-C₆ alkylamino C₁-C₆ alkyl group whereinthe alkyl groups are the same or different, 25e) a phenyl group, 26e) asubstituted phenyl group having, on the ring, one or more, the same ordifferent substituents selected from a) a halogen atom, b) a cyanogroup, c) a nitro group, d) a C₁-C₆ alkyl group, e) a halo C₁-C₆ alkylgroup, f) a C₁-C₆ alkoxy group, g) a halo C₁-C₆ alkoxy group, h) a C₁-C₆alkylthio group, i) a halo C₁-C₆ alkylthio group, j) a C₁-C₆alkylsulfinyl group, k) a halo C₁-C₆ alkylsulfinyl group, l) a C₁-C₆alkylsulfonyl group, m) a halo C₁-C₆ alkylsulfonyl group, n) a monoC₁-C₆ alkylamino group, o) a di C₁-C₆ alkylamino group wherein the alkylgroups are the same or different, and p) a C₁-C₆ alkoxycarbonyl group;Y² may be the same or different and is 1f) a hydrogen atom, 2f) ahalogen atom, 3f) a cyano group, 4f) a nitro group, 5f) a hydroxylgroup, 6f) a mercapto group, 7f) an amino group, 8f) a carboxyl group,9f) a C₁-C₆ alkyl group, 10f) a halo C₁-C₆ alkyl group, 11f) a C₂-C₆alkenyl group, 12f) a halo C₂-C₆ alkenyl group, 13f) a C₂-C₆ alkynylgroup, 14f) a halo C₂-C₆ alkynyl group, 15f) a tri C₁-C₆ alkylsilylC₂-C₆ alkynyl group wherein the alkyl groups are the same or different,16f) a phenyl C₂-C₆ alkynyl group, 17f) a C₁-C₆ alkoxy C₁-C₆ alkoxyC₁-C₆ alkyl group, 18f) a hydroxy C₁-C₆ alkyl group, 19f) a C₁-C₆alkylcarbonyloxy C₁-C₆ alkyl group, 20f) a C₃-C₆ cycloalkyl group, 21f)a halo C₃-C₆ cycloalkyl group, 22f) a C₃-C₆ cycloalkyl C₁-C₆ alkylgroup, 23f) a halo C₃-C₆ cycloalkyl C₁-C₆ alkyl group, 24f) a C₁-C₆alkoxy group, 25f) a halo C₁-C₆ alkoxy group, 26f) a C₁-C₆ alkoxy C₁-C₆alkoxy group, 27f) a halo C₁-C₆ alkoxy C₁-C₆ alkoxy group, 28f) a phenylC₁-C₆ alkoxy group, 29f) a C₁-C₆ alkoxy C₁-C₆ alkyl group, 30f) a haloC₁-C₆ alkoxy C₁-C₆ alkyl group, 31f) a C₁-C₆ alkylthio group, 32f) ahalo C₁-C₆ alkylthio group, 33f) a C₁-C₆ alkylsulfinyl group, 34f) ahalo C₁-C₆ alkylsulfinyl group, 35f) a C₁-C₆ alkylsulfonyl group, 36f) ahalo C₁-C₆ alkylsulfonyl group, 37f) a C₁-C₆ alkylthio C₁-C₆ alkylgroup, 38f) a halo C₁-C₆ alkylthio C₁-C₆ alkyl group, 39f) a C₁-C₆alkylsulfinyl C₁-C₆ alkyl group, 40f) a halo C₁-C₆ alkylsulfinyl C₁-C₆alkyl group, 41f) a C₁-C₆ alkylsulfonyl C₁-C₆ alkyl group, 42f) a haloC₁-C₆ alkylsulfonyl C₁-C₆ alkyl group, 43f) a mono C₁-C₆ alkylaminogroup, 44f) a di C₁-C₆ alkylamino group wherein the alkyl groups are thesame or different, 45f) a phenylamino group, 46f) a mono C₁-C₆alkylamino C₁-C₆ alkyl group, 47f) a di C₁-C₆ alkylamino C₁-C₆ alkylgroup wherein the alkyl groups are the same or different, 48f) a phenylgroup, 49f) a substituted phenyl group having, on the ring, one or more,the same or different substituents selected from a) a halogen atom, b) acyano group, c) a nitro group, d) a C₁-C₆ alkyl group, e) a halo C₁-C₆alkyl group, f) a C₁-C₆ alkoxy group, g) a halo C₁-C₆ alkoxy group, h) aC₁-C₆ alkylthio group, i) a halo C₁-C₆ alkylthio group, j) a C₁-C₆alkylsulfinyl group, k) a halo C₁-C₆ alkylsulfinyl group, l) a C₁-C₆alkylsulfonyl group, m) a halo C₁-C₆ alkylsulfonyl group, n) a monoC₁-C₆ alkylamino group, o) a di C₁-C₆ alkylamino group wherein the alkylgroups are the same or different, and p) a C₁-C₆ alkoxycarbonyl group,50f) a phenoxy group, 51f) a substituted phenoxy group having, on thering, one or more, the same or different substituents selected from a) ahalogen atom, b) a cyano group, c) a nitro group, d) a C₁-C₆ alkylgroup, e) a halo C₁-C₆ alkyl group, f) a C₁-C₆ alkoxy group, g) a haloC₁-C₆ alkoxy group, h) a C₁-C₆ alkylthio group, i) a halo C₁-C₆alkylthio group, j) a C₁-C₆ alkylsulfinyl group, k) a halo C₁-C₆alkylsulfinyl group, l) a C₁-C₆ alkylsulfonyl group, m) a halo C₁-C₆alkylsulfonyl group, n) a mono C₁-C₆ alkylamino group, o) a di C₁-C₆alkylamino group wherein the alkyl groups are the same or different, andp) a C₁-C₆ alkoxycarbonyl group, 52f) a heterocyclic group, or 53f) asubstituted heterocyclic group having, on the ring, one or more, thesame or different substituents selected from a) a halogen atom, b) acyano group, c) a nitro group, d) a C₁-C₆ alkyl group, e) a halo C₁-C₆alkyl group, f) a C₁-C₆ alkoxy group, g) a halo C₁-C₆ alkoxy group, h) aC₁-C₆ alkylthio group, i) a halo C₁-C₆ alkylthio group, j) a C₁-C₆alkylsulfinyl group, k) a halo C₁-C₆ alkylsulfinyl group, l) a C₁-C₆alkylsulfonyl group, m) a halo C₁-C₆ alkylsulfonyl group, n) a monoC₁-C₆ alkylamino group, o) a di C₁-C₆ alkylamino group wherein the alkylgroups are the same or different, and p) a C₁-C₆ alkoxycarbonyl group; mis 1 or 2; and n is an integer of 1-3, or a salt thereof.
 2. Thesubstituted pyrazolecarboxanilide derivative of claim 1, wherein R¹ is1a) a hydrogen atom, 2a) a C₁-C₆ alkyl group, 3a) a halo C₁-C₆ alkylgroup, 4a) a C₁-C₆ alkylcarbonyl group, 5a) a halo C₁-C₆ alkylcarbonylgroup, 6a) a C₂-C₆ alkenylcarbonyl group, 13a) a C₂-C₆ alkenyl group,17a) a C₁-C₁₀ alkoxy C₁-C₆ alkyl group, 18a) a halo C₁-C₆ alkoxy C₁-C₆alkyl group, 19a) a C₂-C₆ alkenyloxy C₁-C₆ alkyl group, 20a) a C₁-C₆alkoxy C₁-C₆ alkoxy C₁-C₆ alkyl group, 29a) a phenyl C₁-C₆ alkoxy C₁-C₆alkyl group, 30a) a substituted phenyl C₁-C₆ alkoxy C₁-C₆ alkyl grouphaving, on the ring, one or more, the same or different substituentsselected from a) a halogen atom, b) a cyano group, c) a nitro group, d)a C₁-C₆ alkyl group, e) a halo C₁-C₆ alkyl group, f) a C₁-C₆ alkoxygroup, g) a halo C₁-C₆ alkoxy group, h) a C₁-C₆ alkylthio group, i) ahalo C₁-C₆ alkylthio group, j) a C₁-C₆ alkylsulfinyl group, k) a haloC₁-C₆ alkylsulfinyl group, l) a C₁-C₆ alkylsulfonyl group, m) a haloC₁-C₆ alkylsulfonyl group, n) a mono C₁-C₆ alkylamino group, o) a diC₁-C₆ alkylamino group wherein the alkyl groups are the same ordifferent, and p) a C₁-C₆ alkoxycarbonyl group, 31a) a C₁-C₁₆alkoxycarbonyl group, 32a) a C₁-C₆ alkoxy C₁-C₆ alkoxycarbonyl group,33a) a halo C₁-C₆ alkoxycarbonyl group, 34a) a C₂-C₆ alkenyloxycarbonylgroup, 35a) a C₁-C₆ alkylthiocarbonyl group, 42a) a phenyl C₁-C₆ alkylgroup, 43a) a substituted phenyl C₁-C₆ alkyl group having, on the ring,one or more, the same or different substituents selected from a) ahalogen atom, b) a cyano group, c) a nitro group, d) a C₁-C₆ alkylgroup, e) a halo C₁-C₆ alkyl group, f) a C₁-C₆ alkoxy group, g) a haloC₁-C₆ alkoxy group, h) a C₁-C₆ alkylthio group, i) a halo C₁-C₆alkylthio group, j) a C₁-C₆ alkylsulfinyl group, k) a halo C₁-C₆alkylsulfinyl group, l) a C₁-C₆ alkylsulfonyl group, m) a halo C₁-C₆alkylsulfonyl group, n) a mono C₁-C₆ alkylamino group, o) a di C₁-C₆alkylamino group wherein the alkyl groups are the same or different, andp) a C₁-C₆ alkoxycarbonyl group, 44a) a phenylcarbonyl group, 45a) asubstituted phenylcarbonyl group having, on the ring, one or more, thesame or different substituents selected from a) a halogen atom, b) acyano group, c) a nitro group, d) a C₁-C₆ alkyl group, e) a halo C₁-C₆alkyl group, f) a C₁-C₆ alkoxy group, g) a halo C₁-C₆ alkoxy group, h) aC₁-C₆ alkylthio group, i) a halo C₁-C₆ alkylthio group, j) a C₁-C₆alkylsulfinyl group, k) a halo C₁-C₆ alkylsulfinyl group, l) a C₁-C₆alkylsulfonyl group, m) a halo C₁-C₆ alkylsulfonyl group, n) a monoC₁-C₆ alkylamino group, o) a di C₁-C₆ alkylamino group wherein the alkylgroups are the same or different, and p) a C₁-C₆ alkoxycarbonyl group,46a) a heterocyclylcarbonyl group, 47a) a substitutedheterocyclylcarbonyl group having, on the ring, one or more, the same ordifferent substituents selected from a) a halogen atom, b) a cyanogroup, c) a nitro group, d) a C₁-C₆ alkyl group, e) a halo C₁-C₆ alkylgroup, f) a C₁-C₆ alkoxy group, g) a halo C₁-C₆ alkoxy group, h) a C₁-C₆alkylthio group, i) a halo C₁-C₆ alkylthio group, j) a C₁-C₆alkylsulfinyl group, k) a halo C₁-C₆ alkylsulfinyl group, l) a C₁-C₆alkylsulfonyl group, m) a halo C₁-C₆ alkylsulfonyl group, n) a monoC₁-C₆ alkylamino group, o) a di C₁-C₆ alkylamino group wherein the alkylgroups are the same or different, and p) a C₁-C₆ alkoxycarbonyl group,48a) a phenoxycarbonyl group, 49a) a substituted phenoxycarbonyl grouphaving, on the ring, one or more, the same or different substituentsselected from a) a halogen atom, b) a cyano group, c) a nitro group, d)a C₁-C₆ alkyl group, e) a halo C₁-C₆ alkyl group, f) a C₁-C₆ alkoxygroup, g) a halo C₁-C₆ alkoxy group, h) a C₁-C₆ alkylthio group, i) ahalo C₁-C₆ alkylthio group, j) a C₁-C₆ alkylsulfinyl group, k) a haloC₁-C₆ alkylsulfinyl group, l) a C₁-C₆ alkylsulfonyl group, m) a haloC₁-C₆ alkylsulfonyl group, n) a mono C₁-C₆ alkylamino group, o) a diC₁-C₆ alkylamino group wherein the alkyl groups are the same ordifferent, and p) a C₁-C₆ alkoxycarbonyl group, 50a) a phenoxy C₁-C₆alkylcarbonyl group, 51a) a substituted phenoxy C₁-C₆ alkylcarbonylgroup having, on the ring, one or more, the same or differentsubstituents selected from a) a halogen atom, b) a cyano group, c) anitro group, d) a C₁-C₆ alkyl group, e) a halo C₁-C₆ alkyl group, f) aC₁-C₆ alkoxy group, g) a halo C₁-C₆ alkoxy group, h) a C₁-C₆ alkylthiogroup, i) a halo C₁-C₆ alkylthio group, j) a C₁-C₆ alkylsulfinyl group,k) a halo C₁-C₆ alkylsulfinyl group, l) a C₁-C₆ alkylsulfonyl group, m)a halo C₁-C₆ alkylsulfonyl group, n) a mono C₁-C₆ alkylamino group, o) adi C₁-C₆ alkylamino group wherein the alkyl groups are the same ordifferent, and p) a C₁-C₆ alkoxycarbonyl group, 52a) a phenylsulfonylgroup, 53a) a substituted phenylsulfonyl group having, on the ring, oneor more, the same or different substituents selected from a) a halogenatom, b) a cyano group, c) a nitro group, d) a C₁-C₆ alkyl group, e) ahalo C₁-C₆ alkyl group, f) a C₁-C₆ alkoxy group, g) a halo C₁-C₆ alkoxygroup, h) a C₁-C₆ alkylthio group, i) a halo C₁-C₆ alkylthio group, j) aC₁-C₆ alkylsulfinyl group, k) a halo C₁-C₆ alkylsulfinyl group, l) aC₁-C₆ alkylsulfonyl group, m) a halo C₁-C₆ alkylsulfonyl group, n) amono C₁-C₆ alkylamino group, o) a di C₁-C₆ alkylamino group wherein thealkyl groups are the same or different, and p) a C₁-C₆ alkoxycarbonylgroup, 58a) a di C₁-C₆ alkylaminothio group wherein the alkyl groups arethe same or different, 59a) a C₃-C₆ cycloalkylcarbonyl group, 61a) aC₁-C₆ alkyl C₃-C₆ cycloalkylcarbonyl group, 63a) a phenyl C₁-C₆alkylcarbonyl group, 64a) a substituted phenyl C₁-C₆ alkylcarbonyl grouphaving, on the ring, one or more, the same or different substituentsselected from a) a halogen atom, b) a cyano group, c) a nitro group, d)a C₁-C₆ alkyl group, e) a halo C₁-C₆ alkyl group, f) a C₁-C₆ alkoxygroup, g) a halo C₁-C₆ alkoxy group, h) a C₁-C₆ alkylthio group, i) ahalo C₁-C₆ alkylthio group, j) a C₁-C₆ alkylsulfinyl group, k) a haloC₁-C₆ alkylsulfinyl group, l) a C₁-C₆ alkylsulfonyl group, m) a haloC₁-C₆ alkylsulfonyl group, n) a mono C₁-C₆ alkylamino group, o) a diC₁-C₆ alkylamino group wherein the alkyl groups are the same ordifferent, and p) a C₁-C₆ alkoxycarbonyl group, 65a) a phenyl C₃-C₆cycloalkylcarbonyl group, 66a) a substituted phenyl C₃-C₆cycloalkylcarbonyl group having, on the ring, one or more, the same ordifferent substituents selected from a) a halogen atom, b) a cyanogroup, c) a nitro group, d) a C₁-C₆ alkyl group, e) a halo C₁-C₆ alkylgroup, f) a C₁-C₆ alkoxy group, g) a halo C₁-C₆ alkoxy group, h) a C₁-C₆alkylthio group, i) a halo C₁-C₆ alkylthio group, j) a C₁-C₆alkylsulfinyl group, k) a halo C₁-C₆ alkylsulfinyl group, l) a C₁-C₆alkylsulfonyl group, m) a halo C₁-C₆ alkylsulfonyl group, n) a monoC₁-C₆ alkylamino group, o) a di C₁-C₆ alkylamino group wherein the alkylgroups are the same or different, and p) a C₁-C₆ alkoxycarbonyl group,68a) a C₁-C₆ alkoxy C₁-C₆ alkylcarbonyl group, 73a) a C₁-C₆alkylcarbonyl C₁-C₆ alkylcarbonyl group, or 74a) a C₁-C₆ alkoxycarbonylC₁-C₆ alkylcarbonyl group, or a salt thereof.
 3. The substitutedpyrazolecarboxanilide derivative of claim 1, wherein R² is 1b) ahydrogen atom, 2b) a halogen atom, 6b) a hydroxy group, 7b) a C₁-C₆alkoxy group, or 8b) a halo C₁-C₆ alkoxy group, or a salt thereof. 4.The substituted pyrazolecarboxanilide derivative of claim 1, wherein Gis 1c) a C₂-C₁₀ alkyl group, 3c) a C₃-C₁₀ alkenyl group, or 11c) a C₃-C₈cycloalkyl C₁-C₆ alkyl group, or a salt thereof.
 5. The substitutedpyrazolecarboxanilide derivative of claim 1, wherein X is 1d) a hydrogenatom, 2d) a halogen atom, or 5d) a C₁-C₆ alkyl group, or a salt thereof.6. The substituted pyrazolecarboxanilide derivative of claim 1, whereinZ is an oxygen atom; Y¹ is 2e) a C₁-C₆ alkyl group, 3e) a halo C₁-C₆alkyl group, or 4e) a C₂-C₆ alkenyl group; and Y² is 1f) a hydrogenatom, 2f) a halogen atom, 9f) a C₁-C₆ alkyl group, 10f) a halo C₁-C₆alkyl group, or 31f) a C₁-C₆ alkylthio group, or a salt thereof.
 7. Thesubstituted pyrazolecarboxanilide derivative of claim 1, wherein R¹ is1a) a hydrogen atom, 4a) a C₁-C₆ alkylcarbonyl group, 5a) a halo C₁-C₆alkylcarbonyl group, 17a) a C₁-C₁₀ alkoxy C₁-C₆ alkyl group, 18a) a haloC₁-C₆ alkoxy C₁-C₆ alkyl group, 31a) a C₁-C₁₆ alkoxycarbonyl group, 33a)a halo C₁-C₆ alkoxycarbonyl group, or 68a) a C₁-C₆ alkoxy C₁-C₆alkylcarbonyl group; R² is 1b) a hydrogen atom, or 7b) a C₁-C₆ alkoxygroup; G is 1c) a C₂-C₁₀ alkyl group; Z is an oxygen atom; X is 1d) ahydrogen atom; Y¹ is 2e) a C₁-C₆ alkyl group; and Y² may be the same ordifferent and is 1f) a hydrogen atom, 2f) a halogen atom, 9f) a C₁-C₆alkyl group, or 10f) a halo C₁-C₆ alkyl group, or a salt thereof.
 8. Anagrohorticultural agent comprising a substituted pyrazolecarboxanilidederivative of claim 1 or a salt thereof as an active ingredient.
 9. Theagrohorticultural agent of claim 8, which is an agrohorticulturalinsecticide or acaricide.
 10. A method of using an agrohorticulturalagent, which comprises treating a target plant or soil with an effectiveamount of an agrohorticultural agent of claim 8 so as to control noxiousorganisms from useful plants.
 11. A substituted aniline derivativerepresented by the formula (II):

wherein R¹ is 1a) a hydrogen atom, 2a) a C₁-C₈ alkyl group, 3a) a haloC₁-C₆ alkyl group, 4a) a C₁-C₆ alkylcarbonyl group, 5a) a halo C₁-C₆alkylcarbonyl group, 6a) a C₂-C₆ alkenylcarbonyl group, 7a) a halo C₂-C₆alkenylcarbonyl group, 8a) a C₁-C₆ alkylcarbonyl C₁-C₆ alkyl group, 9a)a C₃-C₆ cycloalkyl group, 10a) a halo C₃-C₆ cycloalkyl group, 11a) aC₃-C₆ cycloalkyl C₁-C₆ alkyl group, 12a) a halo C₃-C₆ cycloalkyl C₁-C₆alkyl group, 13a) a C₂-C₆ alkenyl group, 14a) a halo C₂-C₆ alkenylgroup, 15a) a C₂-C₆ alkynyl group, 16a) a halo C₂-C₆ alkynyl group, 17a)a C₁-C₁₀ alkoxy C₁-C₆ alkyl group, 18a) a halo C₁-C₆ alkoxy C₁-C₆ alkylgroup, 19a) a C₂-C₆ alkenyloxy C₁-C₆ alkyl group, 20a) a C₁-C₆ alkoxyC₁-C₆ alkoxy C₁-C₆ alkyl group, 21a) a C₁-C₆ alkylthio C₁-C₆ alkylgroup, 22a) a halo C₁-C₆ alkylthio C₁-C₆ alkyl group, 23a) a C₁-C₆alkylsulfinyl C₁-C₆ alkyl group, 24a) a halo C₁-C₆ alkylsulfinyl C₁-C₆alkyl group, 25a) a C₁-C₆ alkylsulfonyl C₁-C₆ alkyl group, 26a) a haloC₁-C₆ alkylsulfonyl C₁-C₆ alkyl group, 27a) a mono C₁-C₆ alkylaminoC₁-C₆ alkyl group, 28a) a di C₁-C₆ alkylamino C₁-C₆ alkyl group whereinthe alkyl groups are the same or different, 29a) a phenyl C₁-C₆ alkoxyC₁-C₆ alkyl group, 30a) a substituted phenyl C₁-C₆ alkoxy C₁-C₆ alkylgroup having, on the ring, one or more, the same or differentsubstituents selected from a) a halogen atom, b) a cyano group, c) anitro group, d) a C₁-C₆ alkyl group, e) a halo C₁-C₆ alkyl group, f) aC₁-C₆ alkoxy group, g) a halo C₁-C₆ alkoxy group, h) a C₁-C₆ alkylthiogroup, i) a halo C₁-C₆ alkylthio group, j) a C₁-C₆ alkylsulfinyl group,k) a halo C₁-C₆ alkylsulfinyl group, l) a C₁-C₆ alkylsulfonyl group, m)a halo C₁-C₆ alkylsulfonyl group, n) a mono C₁-C₆ alkylamino group, o) adi C₁-C₆ alkylamino group wherein the alkyl groups are the same ordifferent, and p) a C₁-C₆ alkoxycarbonyl group, 31a) a C₁-C₁₆alkoxycarbonyl group, 32a) a C₁-C₆ alkoxy C₁-C₆ alkoxycarbonyl group,33a) a halo C₁-C₆ alkoxycarbonyl group, 34a) a C₂-C₆ alkenyloxycarbonylgroup, 35a) a C₁-C₆ alkylthiocarbonyl group, 36a) a mono C₁-C₆alkylaminocarbonyl group, 37a) a di C₁-C₆ alkylaminocarbonyl groupwherein the alkyl groups are the same or different, 38a) a C₁-C₆alkoxycarbonyl C₁-C₆ alkyl group, 39a) a C₁-C₆ alkylsulfonyl group, 40a)a halo C₁-C₆ alkylsulfonyl group, 41a) a cyano C₁-C₆ alkyl group, 42a) aphenyl C₁-C₆ alkyl group, 43a) a substituted phenyl C₁-C₆ alkyl grouphaving, on the ring, one or more, the same or different substituentsselected from a) a halogen atom, b) a cyano group, c) a nitro group, d)a C₁-C₆ alkyl group, e) a halo C₁-C₆ alkyl group, f) a C₁-C₆ alkoxygroup, g) a halo C₁-C₆ alkoxy group, h) a C₁-C₆ alkylthio group, i) ahalo C₁-C₆ alkylthio group, j) a C₁-C₆ alkylsulfinyl group, k) a haloC₁-C₆ alkylsulfinyl group, l) a C₁-C₆ alkylsulfonyl group, m) a haloC₁-C₆ alkylsulfonyl group, n) a mono C₁-C₆ alkylamino group, o) a diC₁-C₆ alkylamino group wherein the alkyl groups are the same ordifferent, and p) a C₁-C₆ alkoxycarbonyl group, 44a) a phenylcarbonylgroup, 45a) a substituted phenylcarbonyl group having, on the ring, oneor more, the same or different substituents selected from a) a halogenatom, b) a cyano group, c) a nitro group, d) a C₁-C₆ alkyl group, e) ahalo C₁-C₆ alkyl group, f) a C₁-C₆ alkoxy group, g) a halo C₁-C₆ alkoxygroup, h) a C₁-C₆ alkylthio group, i) a halo C₁-C₆ alkylthio group, j) aC₁-C₆ alkylsulfinyl group, k) a halo C₁-C₆ alkylsulfinyl group, l) aC₁-C₆ alkylsulfonyl group, m) a halo C₁-C₆ alkylsulfonyl group, n) amono C₁-C₆ alkylamino group, o) a di C₁-C₆ alkylamino group wherein thealkyl groups are the same or different, and p) a C₁-C₆ alkoxycarbonylgroup, 46a) a heterocyclylcarbonyl group, 47a) a substitutedheterocyclylcarbonyl group having, on the ring, one or more, the same ordifferent substituents selected from a) a halogen atom, b) a cyanogroup, c) a nitro group, d) a C₁-C₆ alkyl group, e) a halo C₁-C₆ alkylgroup, f) a C₁-C₆ alkoxy group, g) a halo C₁-C₆ alkoxy group, h) a C₁-C₆alkylthio group, i) a halo C₁-C₆ alkylthio group, j) a C₁-C₆alkylsulfinyl group, k) a halo C₁-C₆ alkylsulfinyl group, l) a C₁-C₆alkylsulfonyl group, m) a halo C₁-C₆ alkylsulfonyl group, n) a monoC₁-C₆ alkylamino group, o) a di C₁-C₆ alkylamino group wherein the alkylgroups are the same or different, and p) a C₁-C₆ alkoxycarbonyl group,48a) a phenoxycarbonyl group, 49a) a substituted phenoxycarbonyl grouphaving, on the ring, one or more, the same or different substituentsselected from a) a halogen atom, b) a cyano group, c) a nitro group, d)a C₁-C₆ alkyl group, e) a halo C₁-C₆ alkyl group, f) a C₁-C₆ alkoxygroup, g) a halo C₁-C₆ alkoxy group, h) a C₁-C₆ alkylthio group, i) ahalo C₁-C₆ alkylthio group, j) a C₁-C₆ alkylsulfinyl group, k) a haloC₁-C₆ alkylsulfinyl group, l) a C₁-C₆ alkylsulfonyl group, m) a haloC₁-C₆ alkylsulfonyl group, n) a mono C₁-C₆ alkylamino group, o) a diC₁-C₆ alkylamino group wherein the alkyl groups are the same ordifferent, and p) a C₁-C₆ alkoxycarbonyl group, 50a) a phenoxy C₁-C₆alkylcarbonyl group, 51a) a substituted phenoxy C₁-C₆ alkylcarbonylgroup having, on the ring, one or more, the same or differentsubstituents selected from a) a halogen atom, b) a cyano group, c) anitro group, d) a C₁-C₆ alkyl group, e) a halo C₁-C₆ alkyl group, f) aC₁-C₆ alkoxy group, g) a halo C₁-C₆ alkoxy group, h) a C₁-C₆ alkylthiogroup, i) a halo C₁-C₆ alkylthio group, j) a C₁-C₆ alkylsulfinyl group,k) a halo C₁-C₆ alkylsulfinyl group, l) a C₁-C₆ alkylsulfonyl group, m)a halo C₁-C₆ alkylsulfonyl group, n) a mono C₁-C₆ alkylamino group, o) adi C₁-C₆ alkylamino group wherein the alkyl groups are the same ordifferent, and p) a C₁-C₆ alkoxycarbonyl group, 52a) a phenylsulfonylgroup, 53a) a substituted phenylsulfonyl group having, on the ring, oneor more, the same or different substituents selected from a) a halogenatom, b) a cyano group, c) a nitro group, d) a C₁-C₆ alkyl group, e) ahalo C₁-C₆ alkyl group, f) a C₁-C₆ alkoxy group, g) a halo C₁-C₆ alkoxygroup, h) a C₁-C₆ alkylthio group, i) a halo C₁-C₆ alkylthio group, j) aC₁-C₆ alkylsulfinyl group, k) a halo C₁-C₆ alkylsulfinyl group, l) aC₁-C₆ alkylsulfonyl group, m) a halo C₁-C₆ alkylsulfonyl group, n) amono C₁-C₆ alkylamino group, o) a di C₁-C₆ alkylamino group wherein thealkyl groups are the same or different, and p) a C₁-C₆ alkoxycarbonylgroup, 54a) a di C₁-C₆ alkylphosphono group wherein the alkyl groups arethe same or different, 55a) a di C₁-C₆ alkylphosphonothio group whereinthe alkyl groups are the same or different, 56a) a N—C₁-C₆ alkyl-N—C₁-C₆alkoxycarbonylaminothio group, 57a) a N—C₁-C₆ alkyl-N—C₁-C₆alkoxycarbonyl C₁-C₆ alkylaminothio group, 58a) a di C₁-C₆alkylaminothio group wherein the alkyl groups are the same or different,59a) a C₃-C₆ cycloalkylcarbonyl group, 60a) a halo C₃-C₆cycloalkylcarbonyl group, 61a) a C₁-C₆ alkyl C₃-C₆ cycloalkylcarbonylgroup, 62a) a halo C₁-C₆ alkyl C₃-C₆ cycloalkylcarbonyl group, 63a) aphenyl C₁-C₆ alkylcarbonyl group, 64a) a substituted phenyl C₁-C₆alkylcarbonyl group having, on the ring, one or more, the same ordifferent substituents selected from a) a halogen atom, b) a cyanogroup, c) a nitro group, d) a C₁-C₆ alkyl group, e) a halo C₁-C₆ alkylgroup, f) a C₁-C₆ alkoxy group, g) a halo C₁-C₆ alkoxy group, h) a C₁-C₆alkylthio group, i) a halo C₁-C₆ alkylthio group, j) a C₁-C₆alkylsulfinyl group, k) a halo C₁-C₆ alkylsulfinyl group, l) a C₁-C₆alkylsulfonyl group, m) a halo C₁-C₆ alkylsulfonyl group, n) a monoC₁-C₆ alkylamino group, o) a di C₁-C₆ alkylamino group wherein the alkylgroups are the same or different, and p) a C₁-C₆ alkoxycarbonyl group,65a) a phenyl C₃-C₆ cycloalkylcarbonyl group, 66a) a substituted phenylC₃-C₆ cycloalkylcarbonyl group having, on the ring, one or more, thesame or different substituents selected from a) a halogen atom, b) acyano group, c) a nitro group, d) a C₁-C₆ alkyl group, e) a halo C₁-C₆alkyl group, f) a C₁-C₆ alkoxy group, g) a halo C₁-C₆ alkoxy group, h) aC₁-C₆ alkylthio group, i) a halo C₁-C₆ alkylthio group, j) a C₁-C₆alkylsulfinyl group, k) a halo C₁-C₆ alkylsulfinyl group, l) a C₁-C₆alkylsulfonyl group, m) a halo C₁-C₆ alkylsulfonyl group, n) a monoC₁-C₆ alkylamino group, o) a di C₁-C₆ alkylamino group wherein the alkylgroups are the same or different, and p) a C₁-C₆ alkoxycarbonyl group,67a) a C₃-C₆ cycloalkyl C₁-C₆ alkylcarbonyl group, 68a) a C₁-C₆ alkoxyC₁-C₆ alkylcarbonyl group, 69a) a halo C₃-C₆ cycloalkyl C₁-C₆alkylcarbonyl group, 70a) a phenoxy C₁-C₆ alkoxycarbonyl group, 71a) asubstituted phenoxy C₁-C₆ alkoxycarbonyl group having, on the ring, oneor more, the same or different substituents selected from a) a halogenatom, b) a cyano group, c) a nitro group, d) a C₁-C₆ alkyl group, e) ahalo C₁-C₆ alkyl group, f) a C₁-C₆ alkoxy group, g) a halo C₁-C₆ alkoxygroup, h) a C₁-C₆ alkylthio group, i) a halo C₁-C₆ alkylthio group, j) aC₁-C₆ alkylsulfinyl group, k) a halo C₁-C₆ alkylsulfinyl group, l) aC₁-C₆ alkylsulfonyl group, m) a halo C₁-C₆ alkylsulfonyl group, n) amono C₁-C₆ alkylamino group, o) a di C₁-C₆ alkylamino group wherein thealkyl groups are the same or different, and p) a C₁-C₆ alkoxycarbonylgroup, 72a) a C₁-C₆ alkylcarbonyloxy C₁-C₆ alkyl group, 73a) a C₁-C₆alkylcarbonyl C₁-C₆ alkylcarbonyl group, or 74a) a C₁-C₆ alkoxycarbonylC₁-C₆ alkylcarbonyl group; R² is 1b) a hydrogen atom, 2b) a halogenatom, 3b) a C₁-C₆ alkyl group, 4b) a halo C₁-C₆ alkyl group, 5b) a cyanogroup, 6b) a hydroxy group, 7b) a C₁-C₆ alkoxy group, 8b) a halo C₁-C₆alkoxy group, 9b) a C₁-C₆ alkoxy C₁-C₃ alkoxy group, 10b) a halo C₁-C₆alkoxy C₁-C₃ alkoxy group, 11b) a C₁-C₆ alkylthio C₁-C₃ alkoxy group,12b) a halo C₁-C₆ alkylthio C₁-C₃ alkoxy group, 13b) a C₁-C₆alkylsulfinyl C₁-C₃ alkoxy group, 14b) a halo C₁-C₆ alkylsulfinyl C₁-C₃alkoxy group, 15b) a C₁-C₆ alkylsulfonyl C₁-C₃ alkoxy group, 16b) a haloC₁-C₆ alkylsulfonyl C₁-C₃ alkoxy group, 17b) a mono C₁-C₆ alkylaminoC₁-C₃ alkoxy group, 18b) a di C₁-C₆ alkylamino C₁-C₃ alkoxy groupwherein the alkyl groups are the same or different, 19b) a C₁-C₆alkylthio group, 20b) a halo C₁-C₆ alkylthio group, 21b) a C₁-C₆alkylsulfinyl group, 22b) a halo C₁-C₆ alkylsulfinyl group, 23b) a C₁-C₆alkylsulfonyl group, 24b) a halo C₁-C₆ alkylsulfonyl group, 25b) anamino group, 26b) a mono C₁-C₆ alkylamino group, 27b) a di C₁-C₆alkylamino group wherein the alkyl groups are the same or different,28b) a phenoxy group, 29b) a substituted phenoxy group having, on thering, one or more, the same or different substituents selected from a) ahalogen atom, b) a cyano group, c) a nitro group, d) a C₁-C₆ alkylgroup, e) a halo C₁-C₆ alkyl group, f) a C₁-C₆ alkoxy group, g) a haloC₁-C₆ alkoxy group, h) a C₁-C₆ alkylthio group, i) a halo C₁-C₆alkylthio group, j) a C₁-C₆ alkylsulfinyl group, k) a halo C₁-C₆alkylsulfinyl group, l) a C₁-C₆ alkylsulfonyl group, m) a halo C₁-C₆alkylsulfonyl group, n) a mono C₁-C₆ alkylamino group, o) a di C₁-C₆alkylamino group wherein the alkyl groups are the same or different, andp) a C₁-C₆ alkoxycarbonyl group, 30b) a phenylthio group, 31b) asubstituted phenylthio group having, on the ring, one or more, the sameor different substituents selected from a) a halogen atom, b) a cyanogroup, c) a nitro group, d) a C₁-C₆ alkyl group, e) a halo C₁-C₆ alkylgroup, f) a C₁-C₆ alkoxy group, g) a halo C₁-C₆ alkoxy group, h) a C₁-C₆alkylthio group, i) a halo C₁-C₆ alkylthio group, j) a C₁-C₆alkylsulfinyl group, k) a halo C₁-C₆ alkylsulfinyl group, l) a C₁-C₆alkylsulfonyl group, m) a halo C₁-C₆ alkylsulfonyl group, n) a monoC₁-C₆ alkylamino group, o) a di C₁-C₆ alkylamino group wherein the alkylgroups are the same or different, and p) a C₁-C₆ alkoxycarbonyl group,32b) a phenylsulfinyl group, 33b) a substituted phenylsulfinyl grouphaving, on the ring, one or more, the same or different substituentsselected from a) a halogen atom, b) a cyano group, c) a nitro group, d)a C₁-C₆ alkyl group, e) a halo C₁-C₆ alkyl group, f) a C₁-C₆ alkoxygroup, g) a halo C₁-C₆ alkoxy group, h) a C₁-C₆ alkylthio group, i) ahalo C₁-C₆ alkylthio group, j) a C₁-C₆ alkylsulfinyl group, k) a haloC₁-C₆ alkylsulfinyl group, l) a C₁-C₆ alkylsulfonyl group, m) a haloC₁-C₆ alkylsulfonyl group, n) a mono C₁-C₆ alkylamino group, o) a diC₁-C₆ alkylamino group wherein the alkyl groups are the same ordifferent, and p) a C₁-C₆ alkoxycarbonyl group, 34b) a phenylsulfonylgroup, 35b) a substituted phenylsulfonyl group having, on the ring, oneor more, the same or different substituents selected from a) a halogenatom, b) a cyano group, c) a nitro group, d) a C₁-C₆ alkyl group, e) ahalo C₁-C₆ alkyl group, f) a C₁-C₆ alkoxy group, g) a halo C₁-C₆ alkoxygroup, h) a C₁-C₆ alkylthio group, i) a halo C₁-C₆ alkylthio group, j) aC₁-C₆ alkylsulfinyl group, k) a halo C₁-C₆ alkylsulfinyl group, l) aC₁-C₆ alkylsulfonyl group, m) a halo C₁-C₆ alkylsulfonyl group, n) amono C₁-C₆ alkylamino group, o) a di C₁-C₆ alkylamino group wherein thealkyl groups are the same or different, and p) a C₁-C₆ alkoxycarbonylgroup, 36b) a phenyl C₁-C₆ alkoxy group, or 37b) a substituted phenylC₁-C₆ alkoxy group having, on the ring, one or more, the same ordifferent substituents selected from a) a halogen atom, b) a cyanogroup, c) a nitro group, d) a C₁-C₆ alkyl group, e) a halo C₁-C₆ alkylgroup, f) a C₁-C₆ alkoxy group, g) a halo C₁-C₆ alkoxy group, h) a C₁-C₆alkylthio group, i) a halo C₁-C₆ alkylthio group, j) a C₁-C₆alkylsulfinyl group, k) a halo C₁-C₆ alkylsulfinyl group, l) a C₁-C₆alkylsulfonyl group, m) a halo C₁-C₆ alkylsulfonyl group, n) a monoC₁-C₆ alkylamino group, o) a di C₁-C₆ alkylamino group wherein the alkylgroups are the same or different, and p) a C₁-C₆ alkoxycarbonyl group; Gis 1c) a C₂-C₁₀ alkyl group, 2c) a halo C₂-C₁₀ alkyl group, 3c) a C₃-C₁₀alkenyl group, 4c) a halo C₃-C₁₀ alkenyl group, 5c) a C₃-C₁₀ alkynylgroup, 6c) a halo C₃-C₁₀ alkynyl group, 7c) a C₃-C₁₀ cycloalkyl group,8c) a substituted C₃-C₁₀ cycloalkyl group having, on the ring, one ormore, the same or different substituents selected from a) a halogenatom, b) a C₁-C₆ alkyl group, and c) a halo C₁-C₆ alkyl group, 9c) aC₃-C₁₀ cycloalkenyl group, 10c) a substituted C₃-C₁₀ cycloalkenyl grouphaving, on the ring, one or more, the same or different substituentsselected from a) a halogen atom, b) a C₁-C₆ alkyl group, and c) a haloC₁-C₆ alkyl group, 11c) a C₃-C₈ cycloalkyl C₁-C₆ alkyl group, or 12c) ahalo C₃-C₈ cycloalkyl C₁-C₆ alkyl group; X may be the same or differentand is 1d) a hydrogen atom, 2d) a halogen atom, 3d) a cyano group, 4d) anitro group, 5d) a C₁-C₆ alkyl group, or 6d) a halo C₁-C₆ alkyl group;and n is an integer of 1-3, or a salt thereof.
 12. The substitutedaniline derivative of claim 11, wherein R¹ is 1a) a hydrogen atom, 2a) aC₁-C₆ alkyl group, 3a) a halo C₁-C₆ alkyl group, 4a) a C₁-C₆alkylcarbonyl group, 5a) a halo C₁-C₆ alkylcarbonyl group, 17a) a C₁-C₆alkoxy C₁-C₆ alkyl group, 18a) a halo C₁-C₆ alkoxy C₁-C₆ alkyl group,31a) a C₁-C₁₆ alkoxycarbonyl group, 33a) a halo C₁-C₆ alkoxycarbonylgroup, 44a) a phenylcarbonyl group, or 45a) a substituted phenylcarbonylgroup having, on the ring, one or more, the same or differentsubstituents selected from a) a halogen atom, b) a cyano group, c) anitro group, d) a C₁-C₆ alkyl group, e) a halo C₁-C₆ alkyl group, f) aC₁-C₆ alkoxy group, g) a halo C₁-C₆ alkoxy group, h) a C₁-C₆ alkylthiogroup, i) a halo C₁-C₆ alkylthio group, j) a C₁-C₆ alkylsulfinyl group,k) a halo C₁-C₆ alkylsulfinyl group, l) a C₁-C₆ alkylsulfonyl group, m)a halo C₁-C₆ alkylsulfonyl group, n) a mono C₁-C₆ alkylamino group, o) adi C₁-C₆ alkylamino group wherein the alkyl groups are the same ordifferent, and p) a C₁-C₆ alkoxycarbonyl group; R² is 1b) a hydrogenatom, 2b) a halogen atom, 6b) a hydroxy group, 7b) a C₁-C₆ alkoxy group,or 8b) a halo C₁-C₆ alkoxy group; G is 1c) a C₂-C₁₀ alkyl group; and Xis 1d) a hydrogen atom, or 5d) a C₁-C₆ alkyl group, or a salt thereof.13. 1,3-Dimethyl-5-trifluoromethylpyrazole-4-carboxylic acid or a saltthereof.
 14. A method of using an agrohorticultural agent, whichcomprises treating a target plant or soil with an effective amount of anagrohorticultural agent of claim 9 so as to control noxious organismsfrom useful plants.